cas 63-74-1, Sulfanilamide | Articles data

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Electrochemical Behavior of Azobenzene-4,4'-disulfonamide at Pyrolitic Graphite Electrode
The electrochemical reduction of azobenzene-4,4'-disulfonamide (1), an oxidation product of sulfanilamide, has been studied at Pyrolytic graphite electrode, over a wide pH range of 3.0 to 10.6 in the Britton Robinson buffers, by electrochemical and spectroscopic techniques.Under cyclic voltammetric conditions the 2e-, 2H+ reduction of this compound was found to give hydrazobenzene-4,4'-disulfonamide which has been characterised using IR, mp, mass and NMR spectra.Under controlled potential electrolysis, the presence of two electron withdrawing -SO2NH2 groups was found to cause the slow disproportionation -3 s-1> of the hydrazo compound and sulfanilamide has been found as the major product of reduction.A plausible mechanism for the ECE reduction of 1 is suggested.
Goyal, R. N.,Srivastava, Amit Kumar
p. 205 - 211
(1993)
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Green process synthesis method of sulfanilamide
The invention discloses a green process synthesis method of sulfanilamide, and belongs to the technical field of organic synthesis. The method comprises the following steps: carrying out amination reaction on an acetamidobenzene sulfonyl chloride dry product and ammonia gas in the presence of an anhydrous solvent; the method has the advantages that the solvent can be recycled by adjusting the reaction temperature and changing the process method, the yield is improved, the environment-friendly treatment cost is reduced, the reaction condition is mild, the operation is convenient, and the method is suitable for industrial production; p-acetamidobenzene sulfonyl chloride is prevented from being decomposed when encountering water, side reactions are reduced, and the yield is increased; during subsequent treatment and pH adjustment, a proper acid is used, so that generation of mixed high-salinity wastewater is avoided; ammonia gas is used for replacing ammonia water, so that raw materials are saved, the alkali consumption is reduced by 63%, and no various high-salinity wastewater is generated; operation is simple, automation degree is high, and waste water is little; the yield of the sulfanilamide can be increased, and the yield of the sulfanilamide is increased to 96.2%-98.3%.
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Paragraph 0019

(2021/09/04)

Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture
The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.
Kühl, Nikos,Leuthold, Mila M.,Behnam, Mira A. M.,Klein, Christian D.
supporting information
p. 4567 - 4587
(2021/05/06)

Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines
Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.
Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju
supporting information
p. 1915 - 1923
(2021/02/06)

Hydroboration reduction reaction of aromatic nitro compounds without transition metal catalysis
The invention relates to a hydroboration reduction reaction of aromatic nitro compounds without transition metal catalysis. According to the method, triethyl boron and potassium tert-butoxide are used as catalysts for the first time, and an aromatic nitro compound and pinacol borane which is low in price and easy to obtain can be conveniently catalyzed to be subjected to a hydroboration reduction reaction under mild conditions to prepare aromatic amine products. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient, and reaction is safe. The selective hydroboration reduction reaction of the non-transition metal reagent catalyzed aromatic nitro compound and pinacol borane is realized for the first time, and a practical new reaction strategy is provided for laboratory preparation or industrial production of aromatic amine products.
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Paragraph 0006; 0077-0080

(2021/07/31)

Synthesis of new Copper Catalyst with Pyrazole Based Tridentate Ligand and Study of Its Activity for Azide Alkyne Coupling
Synthesis of new copper catalyst with pyrazole based tridentate ligand and study of its activity for azide alkyne coupling were investigated by researchers. To a solution of acetyl acetone (2.002 g, 20 mmol), 2- nitrophenylhydrazine in ethanol was added five drops of con. HCl and heated at 50° for 1 hour. After confirming the formation of 3, 5-dimethyl-1-(2-nitrophenyl)- 1H-pyrazole by TLC, ice cooled water was added in to the reaction mixture. The precipitate was filtered, washed with water and then hexane. The product formed as yellow precipitate, that precipitate had been filtered by normal filter paper. The product was recrystallized in ethanol. For synthesis, was suspended in 6 mL of deionized and stirred for 4 h until a clear solution was obtained in 50 ml round bottom flask Cu(OAc) 2. The reaction mixture was diluted with water, filtered, washed sequentially with water, methanol and n-hexane. Then dark greenish blue color crystal were formed and used for the reactions. The solid was crystallized in CH2Cl2 to get crystal whose structure was confirmed by single crystal XRD.
Rajeswari, Panneer Selvam,Nagarajan, Rajendran,P, Sujith K,Emmanuvel, Lourdusamy
supporting information

(2020/12/03)

Bio-waste chitosan-derived N-doped CNT-supported Ni nanoparticles for selective hydrogenation of nitroarenes
In this study, a facile method for the synthesis of leach proof and earth-abundant non-noble Ni nanoparticles on N-doped carbon nanotubes is reported. The catalyst was synthesized by an impregnation-carbonization method, wherein a Ni-chitosan complex upon carbonization in a 5% H2/N2 atmosphere at 800 °C yielded Ni-containing N-doped CNTs. Chitosan served as a single source of carbon and nitrogen, and the nanotube growth was facilitated by the in situ formed Ni nanoparticles. The nanocatalyst was thoroughly characterized by several techniques; elemental mapping by SEM and TEM analysis confirmed the uniform distribution of Ni nanoparticles on the surface of N-doped CNTs with an average size in the range of 10-15 nm. The catalyst efficiently reduced a variety of nitroarenes (>99%) into their corresponding amines at a moderate pressure (5 bar) and a comparatively lower temperature (80 °C). Furthermore, the easy recovery of the catalyst using an external magnetic field along with high activity and easy recyclability makes the protocol eco-friendly.
Advani, Jacky H.,Bajaj, Hari C.,Biradar, Ankush V.,Gawande, Manoj B.,Naikwadi, Dhanaji R.,Ravi, Krishnan
p. 10431 - 10440
(2020/09/18)

Amination method of aromatic compound with electron withdrawing group
The invention belongs to the technical field of organic synthesis, and particularly relates to an amination method of an aromatic compound with an electron withdrawing group. The method specifically comprises the following steps: under the catalysis of a titanium silicalite molecular sieve or a titanium silicalite mesoporous material or a mixture of the titanium silicalite molecular sieve and thetitanium silicalite mesoporous material, carrying out chemical reaction on ammonia gas or ammonia water, a hydrogen peroxide solution and an aromatic compound with an electron withdrawing group to obtain the aromatic amine compound. The method for preparing the aromatic amine compound has the advantages of simple process, no toxic solvent, no metal ion residue, high production efficiency, less three wastes and low cost.
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Paragraph 0014; 0019-0020; 0023-0024

(2020/12/30)

Preparation method for coproducing 3-hydroxyacetophenone and crystallized sulfanilamide
The invention discloses a preparation method for co-producing 3-hydroxyacetophenone and crystallized sulfanilamide. The preparation method comprises the following steps: S1, taking 3-hydroxybenzoic acid, p-acetamidobenzenesulfonyl chloride and an acid-binding agent for condensation reaction to obtain a substance A; S2, performing acylating chlorination reaction on the substance A and an acylatingchlorination reagent to obtain a substance B; S3, taking the substance B to react with dimethyl malonate, magnesium chloride and triethylamine to obtain a substance C; S4, carrying out decarboxylationreaction on the substance C and an acidic substance, carrying out primary filtration, carrying out ammonolysis reaction on a primary filter cake and an aminating agent, adding an alkaline substance,carrying out amino deprotection reaction, crystallizing, carrying out secondary filtration, and taking a secondary filter cake to obtain crystallized sulfanilamide; and adjusting the pH value of the secondary filtrate to be less than 7, and crystallizing to obtain 3-hydroxyacetophenone. According to the preparation method, 3-hydroxybenzoic acid and p-acetamidobenzenesulfonyl chloride are taken asraw materials, two substances, namely 3-hydroxyacetophenone and crystallized sulfanilamide, are synchronously prepared, and the yield is relatively good.
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Paragraph 0045; 0047; 0052-0053; 0059; 0064-0065; 0066; 0071

(2020/08/02)

Harnessing Endogenous Formate for Antibacterial Prodrug Activation by in cellulo Ruthenium-Mediated Transfer Hydrogenation Reaction
The abundance and evolving pathogenic behavior of bacterial microorganisms give rise to antibiotic tolerance and resistance which pose a danger to global public health. New therapeutic strategies are needed to keep pace with this growing threat. We propose a novel approach for targeting bacteria by harnessing formate, a cell metabolite found only in particular bacterial species, to activate an antibacterial prodrug and selectively inhibit their growth. This strategy is premised on transfer hydrogenation reaction on a biorthogonal substrate utilizing native formate as the hydride source as a means of uncaging an antibacterial prodrug. Using coordination-directed 3-component assembly to prepare a library of 768 unique Ru–Arene Schiff-base complexes, we identified several candidates that efficiently reduced sulfonyl azide functional group in the presence of formate. This strategy paves the way for a new approach of targeted antibacterial therapy by exploiting unique bacterial metabolites.
Ang, Wee Han,Shen, Linghui,Weng, Cheng
supporting information
p. 9314 - 9318
(2020/04/29)

A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction-carbonylation of nitroarenes
In this work, synthesis of Pd-NHC-γ-Fe2O3-n-butyl-SO3H and its activity as a bifunctional heterogeneous nanocatalyst containing Pd-NHC and acidic functional groups, are described. This newly synthesized nanomagnetic catalyst is fully characterized by different methods such as FT-IR, XPS, TEM, VSM, ICP and TG analysis. At first, the catalytic activity of Pd-NHC-γ-Fe2O3-n-butyl-SO3H is evaluated for the reduction of nitroarenes in aqueous media using NaBH4 as a clean source of hydrogen generation at ambient temperature. Using the promising results obtained from the nitroarene reduction, this catalytic system is used for two one-pot protocols including reduction-Schiff base condensation and reduction-carbonylation of various nitroarenes. In these reactions the in situ formed amines are further reacted with aldehydes to yield imines or carbonylated to amides. The desired products are obtained in good to high yields in the presence of Pd-NHC-γ-Fe2O3-n-butyl-SO3H as a bifunctional catalyst. The catalyst is reused with the aid of a magnetic bar for up to six consecutive cycles without any drastic loss of its catalytic activity.
Sobhani, Sara,Chahkamali, Farhad Omarzehi,Sansano, José Miguel
p. 1362 - 1372
(2019/01/24)

Utilization of a Hydrogen Source from Renewable Lignocellulosic Biomass for Hydrogenation of Nitroarenes
Exploring of hydrogen source from renewable biomass, such as glucose in alkaline solution, for hydrogenation reactions had been studied since 1860s. According to proposed pathway, only small part of hydrogen source in glucose was utilized. Herein, the utilization of a hydrogen source from renewable lignocellulosic biomass, one of the most abundant renewable sources in nature, for a hydrogenation reaction is described. The hydrogenation is demonstrated by reduction of nitroarenes to arylamines in up to 95 % yields. Mechanism studies suggest that the hydrogenation occurs via a hydrogen transformation pathway.
Tan, Fang-Fang,Tang, Kai-Li,Zhang, Ping,Guo, Yan-Jun,Qu, Mengnan,Li, Yang
p. 4189 - 4195
(2019/03/07)

Defect-mediated selective hydrogenation of nitroarenes on nanostructured WS2
Transition metal dichalcogenides (TMDs) are well known catalysts as both bulk and nanoscale materials. Two-dimensional (2-D) TMDs, which contain single- and few-layer nanosheets, are increasingly studied as catalytic materials because of their unique thickness-dependent properties and high surface areas. Here, colloidal 2H-WS2 nanostructures are used as a model 2-D TMD system to understand how high catalytic activity and selectivity can be achieved for useful organic transformations. Free-standing, colloidal 2H-WS2 nanostructures containing few-layer nanosheets are shown to catalyze the selective hydrogenation of a broad scope of substituted nitroarenes to their corresponding aniline derivatives in the presence of other reducible functional groups. Microscopic and computational studies reveal the important roles of sulfur vacancy-rich basal planes and tungsten-terminated edges, which are more abundant in nanostructured 2-D materials than in their bulk counterparts, in enabling the functional group selectivity. At tungsten-terminated edges and on regions of the basal planes having high concentrations of sulfur vacancies, vertical adsorption of the nitroarene is favored, thus facilitating hydrogen transfer exclusively to the nitro group due to geometric effects. At lower sulfur vacancy concentrations on the basal planes, parallel adsorption of the nitroarene is favored, and the nitro group is selectively hydrogenated due to a lower kinetic barrier. These mechanistic insights reveal how the various defect structures and configurations on 2-D TMD nanostructures facilitate functional group selectivity through distinct mechanisms that depend upon the adsorption geometry, which may have important implications for the design of new and enhanced 2-D catalytic materials across a potentially broad scope of reactions.
Sun, Yifan,Darling, Albert J.,Li, Yawei,Fujisawa, Kazunori,Holder, Cameron F.,Liu, He,Janik, Michael J.,Terrones, Mauricio,Schaak, Raymond E.
p. 10310 - 10317
(2019/11/20)

Intensified Crystallization Processes for 1:1 Drug-Drug Cocrystals of Sulfathiazole-Theophylline, and Sulfathiazole-Sulfanilamide
The chemical synthesis and crystallization steps were integrated successfully for directly producing a 1:1 cocrystal of sulfathiazole-theophylline and a 1:1 cocrystal of sulfathiazole-sulfanilamide. The benefits of this process intensification were the reduction of number of steps, and the amount of energy consumption and solvent used. In addition, the overall cocrystal yields by Intensified Method I were much higher than the ones by the conventional method. Intensified Method I also gave high-purity cocrystals of ≥99%. Sulfathiazole not forming cocrystals with sulfanilamide by Intensified Method I was dissolved in the mother liquor by taking advantage of the pH-dependent solubility of sulfathiazole. Cocrystals of both sulfathiazole-theophylline and sulfathiazole-sulfanilamide systems remained stable under conditions of 40 °C and 75% relative humidity for a month.
Yeh, Kuan Lin,Lee, Tu
p. 1339 - 1349
(2018/03/13)

Unravelling 2-aminoquinazolin-4(3: H)-one as an organocatalyst for the chemoselective reduction of nitroarenes
A novel, mild and transition metal-free, 2-aminoquinazolin-4(3H)-one-assisted reduction of nitroarenes employing hydrazine hydrate as reducing agent and potassium carbonate as a base is reported. For the first time, the activation of hydrazine hydrate with an organocatalyst has been explored for reduction reactions. Also for the first time, 2-aminoquinazolin-4(3H)-one and its derivatives have been investigated as hydrogen bonding organocatalysts for the reduction of nitroarenes to anilines. Sensitive functional groups such as sulfonamide, carboxyl, amide and halides were well tolerated in this green methodology with scalability and high chemoselectivity.
Thakur, Maheshwar S.,Nayal, Onkar S.,Rana, Rohit,Kumar, Manoranjan,Sharma, Sushila,Kumar, Neeraj,Maurya, Sushil K.
supporting information
p. 1373 - 1378
(2018/02/06)

N-doped graphitic carbon-improved Co-MoO3 catalysts on ordered mesoporous SBA-15 for chemoselective reduction of nitroarenes
Metallic Co-MoO3 catalysts supported on ordered mesoporous SBA-15 were first prepared through in situ reaction of SBA-15-supported Co-Mo oxides with 1,10-phenanthroline. The resulting Co-MoO3/NC@SBA-15 catalysts with N-doped carbon (NC) exhibited high catalytic activity and chemoselectivity for selective reduction of various functionalized nitroarenes to the corresponding arylamines in ethanol with hydrazine hydrate at near room temperature (30 °C). For reduction of all tested substrates (28 examples), the catalyst could afford a conversion of >99% and arylamine selectivity of >99%. The excellent catalytic performance of the Co-MoO3/NC@SBA-15 was attributed to the Co-Nχ(C)-Mo active sites generated through the interaction between the surface Co-Nχ(C) and MoO3 species, promoting the dissociation of hydrazine molecule into the active H* species for the reduction of nitro groups. After the seventh cycle for reduction of 4-methoxylnitrobenzene, the 2%Co-MoO3/NC@SBA-15 showed little change in catalytic performance, textural properties, size and dispersion of metal species and valence states of elements, indicating high stability and recyclability.
Huang, Haigen,Liang, Xiangcheng,Wang, Xueguang,Sheng, Yao,Chen, Chenju,Zou, Xiujing,Lu, Xionggang
p. 127 - 137
(2018/05/04)

Energy-saving and emission reduction to amino sulfonamide synthesis method and P sulfonamide (by machine translation)
Energy-saving and emission reduction to amino sulfonamide synthesis method and P sulfonamide, which belongs to the field of amino acid synthesis. Synthetic method comprises: in the presence of phosphorus pentoxide, the chlorosulfonic acid with carbon tetrachloride mixture a plurality of times with the acetyl aniline the sulfonation reaction and each time the degassing is carried out after the sulfonation reaction; and then sequentially to the chlorination reaction, amination reaction and the hydrolysis reaction. With chlorosulfonic acid acetyl aniline molar ratio of 2.75 - 3.25: 1, chloro sulfonic acid with carbon tetrachloride of volume ratio of 1: 1.0 - 1.2. Each degassing operation includes: to 0.3 - 0.5 L/min per liter of solution to the reaction solution in the speed of the inert gas and to 0.6 - 1.0 L/min per liter of solution of the air speed. Raw material reaction completely, and chlorosulfonic acid consumption, high product yield, the full recovery of hydrogen chloride, to reduce emissions. Prepared by the above-mentioned synthetic method to amino sulfonamide, environment-friendly process, high purity, low cost. (by machine translation)
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Paragraph 0048-0055; 0056-0064; 0066-0073; 0075-0076; 0078-0

(2018/09/08)

N,N'-bis-substituted aryl thiourea derivatives and synthetic method and application thereof
The invention discloses N,N'-bis-substituted aryl thiourea derivatives which are a series of compounds simultaneously containing various substituted aromatic ring structures and asymmetric substituted thiourea structures and are all novel structural compounds which are not reported in the literature. The biological activity test analysis of all the target compounds includes determination of DPPH antioxidant activity and antiviral activity. Results indicate that, in general, the designed and synthesized compounds are novel in structures and have the antioxidant activity and the antiviral activity revealed for the first time. In addition, the unknown biological activity is not fully elucidated, and thus the compounds are expected to provide a certain material basis for further research and development of new drugs.
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Paragraph 0069; 0072; 0073

(2017/04/26)

Chemoselective Hydrogenation of Nitroarenes Catalyzed by Molybdenum Sulphide Clusters
Herein, we describe an atom efficient and general protocol for the chemoselective hydrogenation of nitroarenes to anilines catalyzed by well-defined diimino and diamino cubane-type Mo3S4 clusters. The novel diimino [Mo3S4Cl3(dnbpy)3]+ ([5]+) (dnbpy=4,4′-dinonyl-2,2′-dipyridyl, L1) trinuclear complex was synthesized in high yields by simple ligand substitution reactions starting from the thiourea (tu) [Mo3S4(tu)8(H2O)]Cl4?4 H2O (3) precursor. This strategy has also been successfully adapted for the isolation of the diamino [Mo3S4Cl3(dmen)3](BF4) ([6](BF4)), (dmen=N,N′-dimethylethylenediamine) salt. Applying these catalysts, high selectivity in the hydrogenation of functionalized nitroarenes has been accomplished. Over thirty anilines bearing synthetically functional groups have been synthesized in 70 to 99 % yield. Notably, the integrity of the cluster core is preserved during catalysis. Based on kinetic studies on the hydrogenation of nitrobenzene and other potential reaction intermediates, the direct reduction to aniline is the preferential route.
Pedrajas, Elena,Sorribes, Iván,Gushchin, Artem L.,Laricheva, Yuliya A.,Junge, Kathrin,Beller, Matthias,Llusar, Rosa
p. 1128 - 1134
(2017/03/27)

Photoinduced Reduction of Nitrobenzenes to Primary Aromatic Amines
Primary aromatic amines were synthesized from the corresponding nitrobenzenes via photoinduced reduction. The reaction was found to be effective when nitrobenzenes with electron-withdrawing substituents were irradiated with a broad band of UV light centered at 306 nm. When reactions are completed, products could be isolated by acid-base extraction or by column chromatography. This presenting photoreaction procedure for the synthesis of primary aromatic amines from the corresponding nitrobenzenes proceeds without the need of a sensitizer in isopropanol or THF. Without the usage of catalysts, or stoichiometric reducing reagent containing heavy metals, this photoinduced reduction of nitrobenzenes fulfils the concept of green chemistry.
Huang, Hua-Hsuan,Chen, Yu-Feng,Niu, Guang-Hao,Chuang, Gary J.
supporting information
p. 1191 - 1194
(2017/06/13)

Bulk iron pyrite as a catalyst for the selective hydrogenation of nitroarenes
Bulk iron pyrite (FeS2) functions as an inexpensive, Earth-abundant, off-the-shelf catalyst capable of selectively hydrogenating a broad scope of substituted nitroarenes to their corresponding aniline derivatives using molecular hydrogen.
Morse, James R.,Callejas, Juan F.,Darling, Albert J.,Schaak, Raymond E.
supporting information
p. 4807 - 4810
(2017/07/11)

The invention relates to a P-chlorobenzene as raw materials synthesis of sulfonamides
The present invention relates to a method for synthesizing sulfanilamide by using chlorobenzene as a raw material. The method for synthesizing sulfanilamide by using chlorobenzene as the raw material is characterized by comprising the following steps: (a) adding ethylene dichloride and ammonium chloride, and dropwise adding chlorosulfonic acid into a reaction vessel, heating the reaction vessel to 50~60 DEG C and dropwise adding chlorobenzene to react continuously for 2~5h, and cooling the reaction vessel to 15~20 DEG C to obtain a first mixed liquid, wherein the mass ratio of the ethylene dichloride, the ammonium chloride, the chlorosulfonic acid and the chlorobenzene is (20~30):1:(20~30):(10~15); and (b) dropwise adding the first mixed liquid into ammonia water with concentration of 22~25%, after stirring and reacting the mixture for 0.5~1 hour, heating the mixture to 40~42 DEG C, continuously stirring and reacting the mixture for 1~2 h; then transferring the mixture to a high pressure reaction vessel, adding a catalyst, heating the mixture to 160~200 DEG C, carrying out reaction for 10~12 h; performing cooling, pressure relieving, steaming out the excess ammonia, adjusting the pH to 6.5~6.7, precipitating the solid, and after filtration and separation, performing drying, wherein the mass ratio of the ammonia water, the catalyst and the chlorobenzene is (120~150):1:(8~15). By using chlorosulfonic acid as sulfonation and sulfonyl chlorination reagents, chlorobenzene sulfonyl chloride can be synthesized in one step, and sulfanilamide can be obtained by ammonolysis. The materials directly enter into a high pressure vessel for ammonolysis without an intermediate separation process, so that the method is relatively short in route, easy to operate and high in total product yield.
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Paragraph 0011-0013

(2017/08/25)

Glucose promoted facile reduction of azides to amines under aqueous alkaline conditions
A quick and efficient method for the reduction of azides to amines in water using d-glucose and KOH as green reagents is reported. The protocol is simple, inexpensive, scalable, and can be applied to different aromatic, heteroaromatic and sulphonyl azides. A high level of chemoselectivity is observed for azide reduction in the presence of other reducible functionalities like cyano, nitro, ether, ketone, amide and acid. The reaction gets completed in a short time (5-20 minutes), and furnishes the amines in high yield (85-99%). Unlike conventional hydrogenations, this reduction protocol does not require any metal catalyst, elaborate experimental setup or use of high-pressure equipment.
Chandna, Nisha,Kaur, Fatehjeet,Kumar, Shobhna,Jain, Nidhi
supporting information
p. 4268 - 4271
(2017/09/29)

Synthesis of N-aryl and N-heteroaryl hydroxylamines via partial reduction of nitroarenes with soluble nanoparticle catalysts
Polystyrene-supported ruthenium nanoparticles enable the selective hydrazine-mediated reduction of nitroarenes to hydroxylamine products in high yield and selectivity. Key to obtaining the hydroxylamine product in good yield was the use of organic solvents capable of solubilizing the polystyrene-supported nanoparticle catalyst. N-aryl and N-heteroaryl hydroxylamines are generated under exceptionally mild conditions and in the presence of a various easily reduced functional groups.
Tyler, Jefferson H.,Nazari, S. Hadi,Patterson, Robert H.,Udumula, Venkatareddy,Smith, Stacey J.,Michaelis, David J.
supporting information
p. 82 - 86
(2016/12/23)

Synthetic method of p-aminobenzenesulfonamide
The invention relates to a synthetic method of p-aminobenzenesulfonamide, which is characterized by successively includes the following steps: (a) adding chlorosulfonic acid into a reaction kettle, controlling the temperature to be 40-50 DEG C, adding acetanilide, increasing the temperature to 55-60 DEG C and performing a reaction for 1-2 h to obtain a first mixture; (b) adding dichloroethane, increasing the temperature to 65-75 DEG C, dropwisely adding a catalyst and SOCl2, and continuously performing the reaction for 1-3 h; (c) controlling the temperature in the reaction kettle to be 15-20 DEG C, dropwisely adding the mixed liquid obtained in the step (b) into ammonia water being 22-25% in mass concentration, stirring the liquid for 0.5-1 h, increasing the temperature to 40-42 DEG C and continuously performing the reaction with stirring for 1-2 h, and filtering the liquid to obtain a crude product of the p-aminobenzenesulfonamide; and (d) adding the crude product in a hydrolysis kettle, adding a NaOH solution being 20-30% in mass concentration, heating the mixture to 90-95 DEG C to perform reflux hydrolysis for 2-3 h, adding an acid solution to regulate the pH value to 6.5-6.7, performing centrifugation, and drying a filter residue to obtain the p-aminobenzenesulfonamide. In the method, the addition quantities of the reactants are accurately controlled so that the use amount of the chlorosulfonic acid is reduced. The method is reduced in cost and is increased in yield and purity of the product.
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Paragraph 0007

(2016/10/17)

Continuous flow hydrogenation of nitroarenes, azides and alkenes using maghemite-Pd nanocomposites
Maghemite-supported ultra-fine Pd (1-3 nm) nanoparticles, prepared by a simple co-precipitation method, find application in the catalytic continuous flow hydrogenation of nitroarenes, azides, and alkenes wherein they play an important role in the reduction of various functional groups on the surface of maghemite with catalyst loading (~6 wt% Pd). The salient features of the protocol include expeditious formation of reduced products in high yields under near ambient conditions with recycling of the catalyst (up to 12 cycles) without any decrease in selectivity and yield.
Rathi, Anuj K.,Gawande, Manoj B.,Ranc, Vaclav,Pechousek, Jiri,Petr, Martin,Cepe, Klara,Varma, Rajender S.,Zboril, Radek
p. 152 - 160
(2015/12/31)

HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES
Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.
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Paragraph 000793

(2016/05/02)

Discovery of a Series of 5,11-Dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-ones as Selective PI3K-δ/γ Inhibitors
Dual inhibition of PI3K-δ and PI3K-γ is an established therapeutic strategy for treatment of hematological malignancies. Reported molecules targeting PI3K-δ/γ selectively are chemically similar and based upon isoquinolin-1(2H)-one or quinazolin-4(3H)-one scaffolds. Here we report a chemically distinct series of potent, selective PI3K-δ/γ inhibitors based on a 5,11-dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one scaffold with comparable biochemical potency and cellular effects on PI3K signaling. We envisage these molecules will provide useful leads for development of next-generation PI3K-δ/γ targeting therapeutics.
Ferguson, Fleur M.,Ni, Jing,Zhang, Tinghu,Tesar, Bethany,Sim, Taebo,Kim, Nam Doo,Deng, Xianming,Brown, Jennifer R.,Zhao, Jean J.,Gray, Nathanael S.
supporting information
p. 908 - 912
(2016/10/22)

(4-Arylsulfamoyl)phenylcarbamic acid esters: I. Synthesis and activity against herpes viruses
Aiming to modify the biological activity of sulfonamides, a number of alkyl (4-arylsulfamoyl)- phenylcarbamates were prepared in 50–70% yield. Biological screening showed that the target compounds possessed a high activity against herpes viruses as well as a traditional antibiotic one.
Krutikov,Erkin,Tets,Shmarov
p. 1567 - 1573
(2016/08/26)

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents
The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.
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Page/Page column 309

(2015/11/16)

Nitrogen-doped graphene-activated iron-oxide-based nanocatalysts for selective transfer hydrogenation of nitroarenes
Nanoscaled iron oxides on carbon were modified with nitrogen-doped graphene (NGr) and found to be excellent catalysts for the chemoselective transfer hydrogenation of nitroarenes to anilines. Under standard reaction conditions, a variety of functionalized and structurally diverse anilines, which serve as key building blocks and central intermediates for fine and bulk chemicals, were synthesized in good to excellent yields.
Jagadeesh, Rajenahally V.,Natte, Kishore,Junge, Henrik,Beller, Matthias
p. 1526 - 1529
(2015/03/14)

Preparation of carbon supported CuPd nanoparticles as novel heterogeneous catalysts for the reduction of nitroarenes and the phosphine-free Suzuki-Miyaura coupling reaction
This paper reports on the synthesis and use of CuPd nanoparticles supported on carbon, as highly active catalysts for the reduction of nitroarenes and Suzuki-Miyaura coupling reactions. The catalyst was characterized using the powder XRD, SEM, ICP-AES and EDS techniques. This method has the advantages of high yields, elimination of homogeneous catalysts, simple methodology and easy work up. Catalytic efficiency remains unaltered even after several repeated cycles.
Nasrollahzadeh, Mahmoud,Jaleh, Babak,Ehsani, Ali
p. 1148 - 1153
(2015/02/19)

Highly selective transfer hydrogenation of functionalised nitroarenes using cobalt-based nanocatalysts
Anilines are important feedstock for the synthesis of a variety of chemicals such as dyes, pigments, pharmaceuticals and agrochemicals. The chemoselective catalytic reduction of nitro compounds represents the most important and prevalent process for the manufacture of functionalized anilines. Consequently, the development of selective catalysts for the reduction of nitro compounds in the presence of other reducible groups is a major challenge and is crucial. In this regard, herein we show that the cobalt oxide (Co3O4-NGr@C) based nano-materials, prepared by the pyrolysis of cobalt-phenanthroline complexes on carbon constitute highly selective catalysts for the transfer hydrogenation of nitroarenes to anilines using formic acid as a hydrogen source. Applying these catalysts, a series of structurally diverse and functionalized nitroarenes have been reduced to anilines with unprecedented chemo-selectivity tolerating halides, olefins, aldehyde, ketone, ester, amide and nitrile functionalities.
Jagadeesh, Rajenahally V.,Banerjee, Debasis,Arockiam, Percia Beatrice,Junge, Henrik,Junge, Kathrin,Pohl, Marga-Martina,Radnik, J?rg,Brückner, Angelika,Beller, Matthias
supporting information
p. 898 - 902
(2015/03/04)

Iridium-catalyzed transfer hydrogenation of nitroarenes to anilines
A simple and general homogeneous catalyst system composed of commercially available [Ir(cod)Cl]2 and 1,10-phenanthroline has been developed for the selective transfer hydrogenation of nitroarenes to anilines. It utilized the readily accessible 2-propanol as a hydrogen donor and had wide substrate scope. A careful mechanistic investigation through real-time detection and a series of controlled experiments with possible intermediates was also carried out, which showed that the transformation proceeds via both phenylhydroxylamine and azobenzene intermediates and the reduction of hydrazobenzene leading to aniline might be the rate-determining step.
Chen, Shujie,Lu, Guoping,Cai, Chun
p. 5360 - 5365
(2015/07/07)

Mild and selective hydrogenation of nitro compounds using palladium nanoparticles supported on amino-functionalized mesocellular foam
We present the utilization of a heterogeneous catalyst comprised of Pd nanoparticles supported on aminopropyl-functionalized siliceous mesocellular foam (Pd0-AmP-MCF) for the selective hydrogenation of aromatic, aliphatic, and heterocyclic nitro compounds to the corresponding amines. In general, the catalytic protocol exclusively affords the desired amine products in excellent yields within short reaction times with the reactions performed at room temperature under ambient pressure of H2. Moreover, the reported Pd nanocatalyst displayed excellent structural integrity for this transformation as it could be recycled multiple times without any observable loss of activity or leaching of metal. In addition, the Pd nanocatalyst could be easily integrated into a continuous-flow device and used for the hydrogenation of 4-nitroanisole on a 2.5 g scale, where the product p-anisidine was obtained in 95% yield within 2 h with a Pd content of less than 1 ppm.
Verho, Oscar,Gustafson, Karl P. J.,Nagendiran, Anuja,Tai, Cheuk-Wai,B?ckvall, Jan-E.
p. 3153 - 3159
(2015/02/03)

Metal-free transfer hydrogenation of nitroarenes in water with vasicine: Revelation of organocatalytic facet of an abundant alkaloid
Vasicine, an abundantly available quinazoline alkaloid from the leaves of Adhatoda vasica, has been successfully employed for metal- and base-free reduction of nitroarenes to the corresponding anilines in water. The method is chemoselective and tolerates a wide range of reducible functional groups, such as ketones, nitriles, esters, halogens, and heterocyclic rings. Dinitroarenes reduced selectively to the corresponding nitroanilines under the present reaction conditions.
Sharma, Sushila,Kumar, Manoranjan,Kumar, Vishal,Kumar, Neeraj
p. 9433 - 9439
(2014/12/11)

PdCu nanoparticles supported on graphene: An efficient and recyclable catalyst for reduction of nitroarenes
Graphene supported PdCu bimetallic nanoparticles were synthesized through coreduction of PdCl2 and CuCl2·H2O. X-ray diffraction (XRD), X-ray photoelectron (XPS) and transmission electron microscopy (TEM) were performed to characterize the structures. The complex could be used as an efficient catalyst for reduction of nitroarenes to the corresponding anilines in the presence of NaBH4 and recycled up to six runs without significant loss of activity.
Feng, Yi-Si,Ma, Jing-Jing,Kang, Yu-Mei,Xu, Hua-Jian
p. 6100 - 6105
(2015/03/30)

Iron and palladium(II) phthalocyanines as recyclable catalysts for reduction of nitroarenes
Iron(II) and palladium(II) phthalocyanines have been established as recyclable heterogeneous catalysts for the reduction of aromatic nitro compounds to corresponding amines using diphenylsilane/sodium borohydride as hydrogen sources in ethanol. Various reducible functional groups, such as acetyl, ester, cyano, amide, sulphonamide and carboxylic acid etc. were well tolerated, and the methods were applicable up to gram scale. Mechanistic studies showed that reduction of nitro group proceed through direct (nitroso) pathway and possibly iron or palladium phthalocyanines activates nitro group for reduction. FePc and PdPc also catalyzed the generation of hydrogen from the combination of diphenylsilane/sodium borohydride and ethanol.
Verma, Praveen Kumar,Bala, Manju,Thakur, Kavita,Sharma, Upendra,Kumar, Neeraj,Singh, Bikram
p. 1258 - 1267
(2014/07/21)

PdCu nanoparticles supported on graphene: An efficient and recyclable catalyst for reduction of nitroarenes
Graphene supported PdCu bimetallic nanoparticles were synthesized through coreduction of PdCl2and CuCl2·H2O. X-ray diffraction (XRD), X-ray photoelectron (XPS) and transmission electron microscopy (TEM) were performed to characterize the structures. The complex could be used as an efficient catalyst for reduction of nitroarenes to the corresponding anilines in the presence of NaBH4and recycled up to six runs without significant loss of activity.
Feng, Yi-Si,Ma, Jing-Jing,Kang, Yu-Mei,Xu, Hua-Jian
p. 6100 - 6105
(2014/12/10)

Solid supported Pd(0): An efficient recyclable heterogeneous catalyst for chemoselective reduction of nitroarenes
Solid supported palladium(0) (SS-Pd) catalyzed highly chemoselective reduction of nitroarenes to the corresponding anilines was accomplished under a milder reaction condition. This catalyst showed high compatibility with various reducing agents (NaBH4, Et3SiH, and NH2NH 2·H2O) and a large number of reducible functional groups such as sulfonamide, amides, carboxylic acid, ester, alcohol, halide, hetero cycle, nitrile, alkene, carbonyl, O-benzyl, and N-benzyl were tolerated. Most of the reactions were clean and high yielding. The SS-Pd catalyst could be recycled up to seven runs without significant loss of activity.
Shil, Arun K.,Sharma, Dharminder,Guha, Nitul Ranjan,Das, Pralay
supporting information; experimental part
p. 4858 - 4861
(2012/09/08)

Zinc phthalocyanine with PEG-400 as a recyclable catalytic system for selective reduction of aromatic nitro compounds
Zinc phthalocyanine with PEG-400 was established as a catalytic system for chemo and regioselective reduction of aromatic nitro compounds to corresponding amines. A large range of reducible functional groups such as acid, amide, ester, halogen, lactone, nitrile, N-benzyl, O-benzyl, hydroxy and heterocycles were well tolerated. Direct synthesis of benzotriazole from O-dinitrobenzene was achieved for the first time. The present catalytic system was successfully employed for the reduction of carbonyl and ester compounds to corresponding alcohols and reductive amination of benzaldehydes with primary amines to form corresponding secondary amines. Remarkable advantages of the present catalytic method include low loading of metal, avoidance of toxic ligands and high isolated yields. The catalyst was recyclable up to four times without any loss of selectivity and activity.
Sharma, Upendra,Kumar, Neeraj,Verma, Praveen Kumar,Kumar, Vishal,Singh, Bikram
supporting information; experimental part
p. 2289 - 2293
(2012/09/10)

Phosphane-free green protocol for selective nitro reduction with an iron-based catalyst
Iron phthalocyanine with iron sulfate has been successfully applied for high chemo- and regioselective reduction of aromatic nitro compounds to give the corresponding amines in a green solvent system without using any toxic ligand. The catalytic systems were also compatible with a large range of other reducible functional groups, such as keto, acid, amide, ester, halogen, lactone, nitrile, N-benzyl, O-benzyl, hydroxy, and heterocycles. In the present study, dinitro compounds have been regioselectively reduced to the corresponding amines with high yield. In most of the cases the conversion and selectivity was greater than 99% as determined by GC-MS analysis. Copyright
Sharma, Upendra,Verma, Praveen Kumar,Kumar, Neeraj,Kumar, Vishal,Bala, Manju,Singh, Bikram
experimental part
p. 5903 - 5907
(2011/06/20)

Novel azo dye compound
A compound represented by formula (I): Formula (I) wherein Z1 is atoms necessary for forming an aromatic ring; Z2 is atoms necessary for forming an aromatic hetero ring; V1 and V2 each are a substituent, and at least one of V1 and V2 is a hydroxyl, primary- or secondary- or tertiary-amino, acylamino, or sulfonamido group; r is 1 to 4; s is 1 to 4; the ring formed by Z1 or Z2 may have a substituent other than V1 or V2; M1 is a counter ion; m1 is the number necessary for neutralizing charge; and X1 and X2 each are a carbon or hetero atom, and at least one of X1 and X2 is a hetero atom.
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Page/Page column 14

(2008/06/13)

Novel azo dye compound
A compound represented by formula (I): Formula (I) wherein Z1 and Z2 each are atoms necessary for forming an aromatic ring; V1 and V2 each are a substituent W1 or W2; when at least one V1 is W1, at least one V2 is W2, or when at least one V1 is W2, at least one V2 is W1; r is 1 to 4; s is 1 to 4; M1 is a counter ion; m1 is the number necessary for neutralizing charge; W1 is a hydroxyl, primary- or secondary- or tertiary-amino, acylamino, or sulfonamido group; W2 is a nitro, cyano, alkoxycarbonyl, aryloxycarbonyl, alkyl- or aryl-sulfonyl, carbamoyl, sulfamoyl, alkenyl, alkynyl, aryl, heterocyclic, sulfo, carboxyl, heterocyclic oxy, ammonio, alkyl- or aryl-sulfinyl, alkyl- or aryl-sulfonyl, acyl, or aryl- or heterocyclic-azo group; and the aromatic ring may have a substituent other than V1 and V2.
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Page/Page column 16-17

(2008/06/13)

Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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(2008/06/13)

BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional hetercyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.
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Page/Page column 264; 265

(2010/02/06)

Selective removal of the N-(tert-butoxycarbonyl) protecting group using H-β zeolite
A simple and efficient protocol for the selective removal of Boc group from nitrogen atom in conjugation with an aromatic system employing H-β zeolite is described.
Tillu, Vasudha H.,Wakharkar, Radhika D.,Pandey, Rajesh K.,Kumar, Pradeep
p. 1004 - 1007
(2007/10/03)

New compounds
The present invention relates to substituted sulfonamide compounds of the general formula (I), wherein P is sulfonamide or amide-substituted sulfonic acid, which compounds are potentially useful for the prophylaxis and treatment of medical conditions relating to obesity, type II diabetes and/or disorders of the central nervous system.
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(2008/06/13)

4-Sulfonamidoanilide tertiary carbinols: A novel series of potassium channel openers
Sulfonamides are viable replacements for the phenylsulfonyl and benzoyl moieties initially described for the anilide tertiary carbinol series of K(ATP) potassium channel openers. The SAR of this new series and the synthetic chemistry employed to generate its members are described.
Empfield,Mayhugh,Ohnmacht,Frank,Grant,Li
p. 775 - 778
(2007/10/03)

Electrochemical investigations on some potential antibacterials, I
Electrochemical behaviour of the medicinally important 4-(4'-sulphonamoyl)hydrazono-1-phenyl-3-methyl-2-pyrazolin-5-ones has been studied at d.m.e. and glassy carbon electrodes. At d.m.e., all six compounds exhibited a single, well-defined, four-electron wave in the pH range 2.5-12.0. Polarographic four-electron wave was found to be diffusion-controlled and irreversible. Similarly, cyclic voltammetry of these compounds at glassy carbon electrode exhibited a single peak. Peak potential sh ows shifts towards negative potential with pH, with linear-segments up to pH 8,2 and are practically pH independent at higher pH values. An anodic peak at far-off positive potential was observed in the reverse scan, indicating the irreversible nature of the electrode process. Controlled potential electrolysis and coulometric studies gave the value of n as 4.0 ± 0.1 in the pH range 2.5 to 10.0. Out of the two major end products formed, one was identified as sulphanilamide and the other as 1-phenyl-3-methyl-4-amino-2-pyrazolin-5-one on the basis of IR and NMR studies. On the basis of DCP, LSV, CV, CPE, coulometry and spectral analysis, a mechanism has been postulated for the reduction of these compounds at d.m.e. and glassy carbon electrodes.
Jain,Damodharan
p. 176 - 180
(2007/10/02)