- p-Tyrosol: a new synthetic method and new types of pharmacological activity
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A new method for the synthesis of p-tyrosol, i.e., 2-(4-hydroxyphenyl)ethanol, has been developed, which considerably simplified the process of preparation of this pharmaceutical substance. The method includes nitration of 2-phenylethanol, catalytic hydrogenation of 2-(4nitrophenyl)ethyl nitrate, and nitrosation of 2-(4-aminophenyl)ethanol, followed by acid hydrolysis of the intermediate diazo compound. The method is easily feasible, furnishes the pharmaceutical substance of high quality, and is quite acceptable for commercialization. Antihypertensive and hemorheologic activities of p-tyrosol in spontaneously hypertensive rats were investigated per se and in combination with captopril. p-Tyrosol in the course administration with captopril was found to enhance the antihypertensive effect of the latter and eliminate its negative effect on red blood cell aggregation.
- Sysolyatin,Kryukov, Yu. A.,Malykhin,Muradov,Chernysheva,Aliev,Smol’yakova,Anishchenko,Sidekhmenova,Shamanaev, A. Yu.,Plotnikov
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Read Online
- Nickel-catalyzed formic acid reductions. A selective method for the reduction of nitro compounds
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Aliphatic and aromatic nitro compounds were selectively reduced to their corresponding amino derivatives in good yields using formic acid and raney nickel. This system is found to be compatible with several sensitive functionalities such as halogens, -OH, -OCH3, -CHO, -COCH3-COC6H5, -COOH, -COOC2H5, -CONH2, -CN, -CH=CH-COOH, -NHCOCH3. The reduction can be carrid out not only with HCOOH but also with HCOONH4.
- Channe Gowda,Prakasha Gowda,Ramesha Baba,Gowda, Shankare
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Read Online
- Thermal dehydration of 2-(4-aminophenyl)ethanol
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The influence of inorganic nucleophilic agents on the liquid-phase process of thermal dehydration of 2-(4-aminophenyl)ethanol at 200-260°C was investigated. It was found that K2CO3, BaCO3, BaO, CaH2, and NaOH did not catalyze the dehydration, but the process takes place easily with the formation of 4-aminostyrene in high yield, using KOH in the range of 100-180 mol % with respect to 2-(4-aminophenyl)ethanol.
- Schul'Tsev
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Read Online
- Palladium supported on metal–organic framework as a catalyst for the hydrogenation of nitroarenes under mild conditions
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Sustainable development demands an environmentally friendly and efficient method for the hydrogenation of organic molecules, including the hydrogenation of functionalized nitroarenes. In this study, a highly active and selective metal–organic framework-supported palladium catalyst was prepared for the catalytic hydrogenation of nitroarenes. High selectivity (>99%) and excellent yield (98%) of aniline were realized after 2 hours in ethanol under hydrogen (1 atm) at room temperature. The reductions were successfully carried out in the presence of a wide range of other reducible functional groups. More importantly, the catalyst was very stable without the loss of its catalytic activity after five cycles.
- Bao, Lingxiang,Fei, Teng,Li, Jiazhe,Pang, Siping,Sun, Chenghui,Yan, Zhiyuan,Yu, Zongbao
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Read Online
- Selective reduction of nitro compounds using CeY zeolite under microwaves
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Aliphatic and aromatic nitro compounds were selectively reduced to their corresponding amino derivatives in good yields using formic acid and CeY zeolite under monomode reactor. This system is found to be compatible with several sensitive functionalities. Beside the recycling result showed it had a long catalyst lifetime and could maintain activity even after being used for 20 cycles.
- Arya, Kapil,Dandia, Anshu
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Read Online
- Direct and practical synthesis of primary anilines through iron-catalyzed C-H bond amination
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The direct C-H amination of arenes is an important strategy to streamline the discovery and preparation of functional molecules. Herein, we report an operationally simple arene C-H amination reaction that, in contrast to most literature precedent, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II)-sulfate serves as a convenient catalyst for the transformation. The reaction tolerates a wide scope of arenes, including structurally complex drugs. Importantly, the arene substrates are used as limiting reagents in the transformation. This operationally simple transformation should considerably accelerate the discovery of medicines and functional molecules.
- Legnani, Luca,Cerai, Gabriele Prina,Morandi, Bill
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Read Online
- Hydrazinium monoformate: A new hydrogen donor. Selective reduction of nitrocompounds catalyzed by commercial zinc dust
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The nitro group in aliphatic and aromatic nitro compounds also containing reducible substituents such as ethene, nitrile, acid, phenol, halogen, ester, etc., are selectively and rapidly reduced at room temperature to corresponding amines in good yields by employing hydrazinium monoformate, in the presence of commercial zinc dust. It was observed that, hydrazinium monoformate is more effective than hydrazine or formic acid and reduction of nitro group occurs without hydrogenolysis in the low cost zinc dust compared to expensive metals like palladium.
- Gowda, Shankare,Gowda, B. K. Kempe,Gowda, D. Channe
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Read Online
- A mild deprotection of trichloroethyl carbamates using indium metal
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The trichloroethoxycarbonyl moiety was efficiently removed from carbamates to furnish the corresponding amines using indium metal in good to excellent yields.
- Mineno, Tomoko,Choi, Seoung-Ryoung,Avery, Mitchell A.
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Read Online
- Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
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Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.
- Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 1618 - 1629
(2021/01/25)
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- Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex
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The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.
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Paragraph 0015
(2021/04/17)
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- Iodinated Choline Transport-Targeted Tracers
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We present a novel series of radioiodinated tracers and potential theranostics for diseases accompanied by pathological function of proteins involved in choline transport. Unlike choline analogues labeled with 11C or 18F that are currently used in the clinic, the iodinated compounds described herein are applicable in positron emission tomography, single-photon emission computed tomography, and potentially in therapy, depending on the iodine isotope selection. Moreover, favorable half-lives of iodine isotopes result in much less challenging synthesis by isotope exchange reaction. Six of the described compounds were nanomolar ligands, and the best compound possessed an affinity 100-fold greater than that of choline. Biodistribution data of 125I-labeled ligands in human prostate carcinoma bearing (PC-3) mice revealed two compounds with a biodistribution profile superior to that of [18F]fluorocholine.
- ?vec, Pavel,Novy, Zbyněk,Ku?ka, Jan,Pet?ík, Milo?,Sedlá?ek, Ond?ej,Kucha?, Martin,Li?ková, Barbora,Medvedíková, Martina,Kolouchová, Kristyna,Groborz, Ond?ej,Loukotová, Lenka,Konefa?, Rafa? ?.,Hajdúch, Marián,Hruby, Martin
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supporting information
p. 15960 - 15978
(2020/12/23)
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- ADENOSINE RECEPTOR BINDING COMPOUNDS
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The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.
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Paragraph 00240
(2020/02/06)
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- Intermediate 4 - amino ethanol synthesis method of synthesis (by machine translation)
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The invention discloses a kind of intermediate 4 - amino ethanol synthesis method, methanol, Pt - SnO2 /C, hydrazine hydrate, to the nitrobenzene ethanol, NaOH, SnCl2 · 2 H2 O, ethylene glycol, carbon black, H2 PtC16 As the main raw material, the synthesis process of the present invention to the nitrobenzene ethanol and hydrazine hydrate in the catalyst Pt - SnO2 Under the action of the/C after reduction to obtain the 4 - amino ethanol; reduction reaction select a low-cost self-made Pt - SnO2 For the reduction of hydrazine hydrate nitrobenzene ethanol/C catalyst, mild reaction conditions, high catalytic efficiency, product purity and yield has reached an ideal effect. (by machine translation)
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Paragraph 0008; 0021-0029
(2018/12/12)
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- A method for preparing the amino ethanol (by machine translation)
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The invention discloses a method for preparing amino ethanol, comprising the following steps: (1) will be soluble in ethyl ether in nitrobenzene acetic acid, heated to 40 - 50 °C, under the protection of nitrogen, adding the hydrogenated lithium aluminum after uniformly mixing and stirring, dripping water, continuing the stirring 3 h, after the reaction is finished, the temperature dropped to 0 °C, add sodium hydroxide solution and water, standing 15 - 20 min after, temperature to room temperature, adding anhydrous MgSO4 , Stirring 20 - 30 min after filtering, the filtrate in the solvent evaporate, made to the nitrobenzene ethanol; (2) the prepared to the nitrobenzene ethanol dissolved in ethanol, adding catalyst, nitrogen, raising the temperature to 80 °C, the hydrogen gas under the atmospheric pressure, the reaction 2 - 3 h, filter after cooling, evaporate the ethanol, the obtained solid recrystallized after, vested the pairs amino ethanol. The application of the preparation method is safe and stable, low demand operating conditions, higher product yield. (by machine translation)
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Paragraph 0019-0057
(2018/06/12)
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- A method of preparing P ethylamine
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The invention discloses a preparation method of p-aminophenylethylamine, belonging to the technical field of organic synthesis. The technical scheme is as follows: the preparation method comprises the following steps: by using p-nitrophenylethanol as a raw material, carrying out catalytic hydrogenation to reduce the para-position nitro groups of the p-nitrophenylethanol into amino groups, carrying out Boc acid anhydride protection on the para-position nitro groups, carrying out substitution reaction on hydroxy groups with sulfonyl chloride compounds to obtain sulfonic acid compounds, aminating, and finally, removing Boc groups to obtain the p-aminophenylethylamine. The preparation process is simple and easy to implement, and has the advantages of cheap and accessible raw materials, higher reaction efficiency and favorable repetitiveness.
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Paragraph 0017; 0018; 0019; 0020; 0021; 0022; 0023; 0024
(2017/04/14)
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- Diethylenetriamine-Mediated Direct Cleavage of Unactivated Carbamates and Ureas
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Diethylenetriamine is effective for the direct cleavage of unactivated carbamates and ureas without additional reagents and catalysts. Various carbamates and ureas were cleaved to afford products in good yield, and the reactions were not affected by air or moisture. Unique chemoselective cleavage of carbamate and urea in the presence of amides was also achieved.
- Noshita, Megumi,Shimizu, Yuhei,Morimoto, Hiroyuki,Ohshima, Takashi
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supporting information
p. 6062 - 6065
(2016/12/09)
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- Enhancement of kinase selectivity in a potent class of arylamide FMS inhibitors
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Structure-activity relationship (SAR) studies on a highly potent series of arylamide FMS inhibitors were carried out with the aim of improving FMS kinase selectivity, particularly over KIT. Potent compound 17r (FMS IC50 0.7 nM, FMS cell IC50 6.1 nM) was discovered that had good PK properties and a greater than fivefold improvement in selectivity for FMS over KIT kinase in a cellular assay relative to the previously reported clinical candidate 4. This improved selectivity was manifested in vivo by no observed decrease in circulating reticulocytes, a measure of bone safety, at the highest studied dose. Compound 17r was highly active in a mouse pharmacodynamic model and demonstrated disease-modifying effects in a dose-dependent manner in a strep cell wall-induced arthritis model of rheumatoid arthritis in rats.
- Illig, Carl R.,Manthey, Carl L.,Meegalla, Sanath K.,Wall, Mark J.,Chen, Jinsheng,Wilson, Kenneth J.,Desjarlais, Renee L.,Ballentine, Shelley K.,Schubert, Carsten,Crysler, Carl S.,Chen, Yanmin,Molloy, Christopher J.,Chaikin, Margery A.,Donatelli, Robert R.,Yurkow, Edward,Zhou, Zhao,Player, Mark R.,Tomczuk, Bruce E.
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p. 6363 - 6369
(2013/11/19)
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- A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system
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Using a system that accelerates the serendipitous discovery of new reactions by evaluating hundreds of DNA-encoded substrate combinations in a single experiment, we explored a broad range of reaction conditions for new bond-forming reactions. We discovered reactivity that led to a biomolecule-compatible, Ru(II)-catalysed azide-reduction reaction induced by visible light. In contrast to current azide-reduction methods, this reaction is highly chemoselective and is compatible with alcohols, phenols, acids, alkenes, alkynes, aldehydes, alkyl halides, alkyl mesylates and disulfides. The remarkable functional group compatibility and mild conditions of the reaction enabled the azide reduction of nucleic acid and oligosaccharide substrates, with no detectable occurrence of side reactions. The reaction was also performed in the presence of a protein enzyme without the loss of enzymatic activity, in contrast to two commonly used azide-reduction methods. The visible-light dependence of this reaction provides a means of photouncaging functional groups, such as amines and carboxylates, on biological macromolecules without using ultraviolet irradiation.
- Chen, Yiyun,Kamlet, Adam S.,Steinman, Jonathan B.,Liu, David R.
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experimental part
p. 146 - 153
(2012/02/17)
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- One-pot system for reduction of epoxides using NaBH4, PdCl 2 catalyst, and moist alumina
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Reduction of epoxides with sodium borohydride, a catalytic amount of palladium(II) chloride, and chromatographic neutral alumina preloaded with a small amount of water (moist alumina) in hexane gave alcohols in good to excellent yields and good selectivity of the desired products under mild conditions. The reaction system was operationally simple and environmentally friendly. The alumina can be recovered simply and reused a number of times without any treatment and with good activity.
- Yakabe, Shigetaka
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experimental part
p. 1339 - 1344
(2010/06/21)
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- An improved bouveault-blanc ester reduction with stabilized alkali metals
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Significantly improved Bouveault-Blanc conditions for ester reduction have been developed using sodium in silica gel (Na-SG), a free-flowing powder that can be easily handled in the open atmosphere. Primary alcohols were prepared in excellent yield from a variety of aliphatic esters under mild reaction conditions. The chemistry presented here is far safer than the classic Bouveault-Blanc reduction and is competitive with more modern hydride reduction methods.
- Bodnar, Brian S.,Vogt, Paul F.
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supporting information; experimental part
p. 2598 - 2600
(2009/08/07)
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- Phase change inks
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Phase change inks comprising a phase change ink carrier and a colorant compound of the formula or wherein R1, R2, R3, R4, R5, m, n, and p are as defined herein, R6 is a direct bond, an alkylene group, an arylene group, an arylalkylene group, or an alkylarylene group, R66 is an alkylene group, an arylene group, an arylalkylene group, or an alkylarylene group, G is a hydroxy group, a carboxylic acid group, an alkyl group having at least about 8 carbon atoms, an aryl group, an arylalkyl group having at least about 14 carbon atoms, an alkylaryl group having at least about 14 carbon atoms, a group of the formula a group of the formula a group of the formula or a group of the formula X is -O- or -NR9-, and R7, R8, and R9 are as defined herein.
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- BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
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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 302
(2010/02/06)
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- Magnesium/ammonium formate promoted rapid, low-cost and selective reduction of nitro compounds
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The reduction of nitro compounds, both aliphatic and aromatic into corresponding amines has been achieved at room temperature in good yields by employing ammonium formate in the presence of low cost magnesium powder. The hydrogenation is fast and selective in the presence of other sensitive functionalities such as halogens, -OH, -OCH3, -CN, -COOR, -COOH etc. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.
- Srinivasa,Abiraj,Gowda, D. Channe
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p. 2882 - 2884
(2007/10/03)
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- Zinc/hydrazine: A low cost-facile system for the reduction of nitro compounds
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The nitro group in aliphatic and aromatic nitro compounds also containing reducible substituents such as ethene, nitrile, carboxylic acid, phenol, halogen, ester etc., are selectively and rapidly reduced at room temperature to corresponding amines in good yields by employing 99-100% hydrazine hydrate, in the presence of commercial zinc dust. It was observed that, this system is equally compatible with existing methods, which employ expensive catalysts like palladium, platinum, ruthenium etc.
- Gowda, Shankare,Gowda, D. Channe
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p. 180 - 183
(2007/10/03)
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- Benzimidazole derivatives
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Compounds, pharmaceutical compositions and methods are provided that are useful in the treatment of inflammatory and immune-related conditions or disorders. In particular, the invention provides compounds which modulate the expression and/or function of proteins involved in inflammation, immune response regulation and cell proliferation. The subject compounds are 2-amino-imidazole derivatives.
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- Indium Mediated Reduction of Nitro and Azide Groups in the Presence of HCl in Aqueous Media
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Indium mediated reduction of azide and nitro groups in the presence of HCl (1.5 equiv based on indium) at room temperature in aqueous THF successfully provided the corresponding amine in high to quantitative yields. Under the some reaction conditions, selective reduction of azide and nitro group in the presence of vinyl group could be accomplished.
- Lee, Jung Gyu,Choi, Kyung Il,Koh, Hun Yeong,Kim, Youseung,Kang, Yonghan,Cho, Yong Seo
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- Zinc-catalyzed ammonium formate reductions: Rapid and selective reduction of aliphatic and aromatic nitro compounds
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Aliphatic and aromatic nitro compounds are selectively and rapidly reduced to their corresponding amino derivatives in good yields using ammonium formate and commercial zinc dust. This system is found to be compatible with several sensitive functionalities such as halogens, -OH, -OCH3, -CHO, -COCH3, -COC6H5, -COOH, COOC2H5, -CONH2, -CN, -CH=CH-COOH, -NHCOCH3. The reduction can be carried out not only with HCOONH4 but also with HCOOH.
- Gowda, D. Channe,Mahesh, B.,Gowda, Shankare
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- Tellurium mediated reduction of aromatic nitro groups
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Treatment of a wide range of aromatic nitro compounds with tellurium powder in aqueous methanolic ammonium chloride results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected.
- Khan, Rabat H.
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p. 290 - 291
(2007/10/03)
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- Ferrocenyl derivatives with one, two, or three sulfur-containing arms for self-assembled monolayer formation
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Self-assembled monolayers of electroactive molecules can form on gold electrodes if the molecules include a sulfur-containing group to coordinate with the gold surface. We have prepared a molecule with a tripod of sulfur groups that has the potential of fixing the geometry of the molecule relative to the gold surface. The target (3) contained the good one-electron donor ferrocene connected through a benzene spacer to an isobutane tripod, with each arm of the tripod ending in a methylthio group. Analogous compounds with one (1) and two (2) coordinating arms were also prepared.
- Hu, Jian,Mattern, Daniell Lewis
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p. 2277 - 2281
(2007/10/03)
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- Synthesis of oligonucleotides containing a new azobenzene fragment with efficient photoisomerizability
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The azobenzene derivatives possessing substituents of ROCH2CH2O- and-CH2CH2OR' or -CONHCH2CH2OR' at p,p'-positions, where R and R' are 4,4'-dimethoxytrityl and 2-cyanoethyl-N,N'-diisopropylphophoramidite, have been synthesized for linking two oligonucelotide segments. It has been found that the azobenzene linkers efficiently undergo trans-cis isomerization by exposing to UV light. The conversion efficiency showed slight dependence on structure or conformation of oligonucleotides attached to the azobenzene chromophore. The cis-form of the azobenzene in oligonucleotides was sufficiently stable at low temperature under dark. The present findings would open the way for light switch of nucleic acid structures. Copyright (C) 1999 Elsevier Science Ltd.
- Yamana, Kazushige,Kan, Katsushi,Nakano, Hidehiko
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p. 2977 - 2983
(2007/10/03)
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- Molecular Armatures. Synthesis and Structure of Troegers Base Analogues Derived from 4-, 2,4-, 3,4-, and 2,4,5-Substituted Aniline Derivatives
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The preparation of biomimetic systems designed to mimic natural receptor sites and enzymic active sites requires the development of new synthetic strategies for preparing large molecules with predictable and well-defined shapes.In this paper a number of derivatives of 6H,12H-5,11-methanodibenzodiazocines are prepared.The scope and limitations of the reaction of formaldehyde with aniline derivatives are examined.The molecules prepared have potential value as conformationally restricted armatures for the construction of biomimetic molecular systems.A crystallographic study reveals that the molecules are folded and that the angle formed by the two aryl rings ranges from 88 deg to 104 deg.Sulfonamides, bromides, alcohols, and amines can be introduced as side-chain substituents in these systems.
- Sucholeiki, Irving,Lynch, Vincent,Phan, Ly,Wilcox, Craig S.
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- TROEGER'S BASE ANALOGS. NEW STRUCTURAL UNITS FOR THE PREPARATION OF CHIRAL HOSTS AND METAL LIGANDS.
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Several Troeger's base analogs are prepared and presented as practical, structurally well defined and unique "folded" armatures for the preparation of chelating or macrocyclic host molecules.
- Wilcox, Craig S.
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p. 5749 - 5752
(2007/10/02)
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- Polybenzimidazole-supported Heterogeneous Palladium Catalysts
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Polybenzimidazole is a useful ligand for the formation of highly active and thermally stable palladium catalysts.
- Li, Nai-Hong,Frechet, Jean M. J.
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p. 1100 - 1101
(2007/10/02)
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- Synthesis of 4-(4-Amidinophenyl)-2-arylsulphonylaminobutyric Acid Amides
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4-(4-Amidinophenyl)-2-arylsulphonylaminobutyric acid amides with differing amide and arylsulphonyl components were synthetized to test their inhibitory activity against serine proteinases.For the purpose of preparing these compounds, β-(4-cyanophenyl)ethylbromide (5) was reacted with acetaminomalonic acid diethyl ester to give 6, the acid hydrolysis of which yielded predominantly 4-(4-carbamoylphenyl)-2-aminobutyric acid (7).The simultaneously formed dicarboxylic acid 9 was separated after N-arylsulphonylation.The reaction of the N-arylsulphonylated acids 10-15 with thionyl chloride afforded acid chlorides (16-18) with a cyano function from which carboxylic acid amides (19-39) were obtained by reaction with diffrent amines.These compounds were converted into the hydroiodides of the compounds named in the title via the thioamides and the thioimidic acid ester hydroiodides.
- Wagner, G.,Vieweg, H.
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- Nucleotide. XIV. Substituierte β-Phenylaethyl-Gruppen. Neue Schutzgruppen fuer Oligonucleotid-Synthesen nach dem Phosphorsaeuretriester-Verfahren
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Various o- and p-substituted β-phenylethanols (2-10) have been synthesized and investigated as blocking groups in the phosphotriester approach.A large number of 5'-O-tritylated thymidine-3'-phosphotriesters (13-36) with two different phosphate protecting groups have been prepared, characterized, and studied according to their chemical stability and usefullness for oligonucleotide syntheses.The combination of a 5'-O-monomethoxytrityl- and a 3'-(2,5-dichlorophenyl, p-nitrophenylethyl)-phosphate function as in 18 turned out to possess optimal properties as a monomeric nucleotide building block due to the fact that these blocking groups can be quantitatively and selectively be removed without harming each other by trifluoroacetic acid in chloroform to 41, by oximate to 42, and by DBU to 43.The base-catalyzed removal of the monosubstituted phenylethyl groups by DBU or DBN respectively as well as the disubstituted phenylethyl groups by triethylamine in aprotic solvents is a β-elimination process leading to phosphodiesters without attack on the P-center.
- Uhlmann, Eugen,Pfleiderer, Wolfgang
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p. 1688 - 1703
(2007/10/02)
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- Manufacture of aromatic amino compounds
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A process for producing an aromatic amine comprises heating an aromatic sulfonate and a metal amide in liquid ammonia in a closed reactor at a temperature of at least 40° C to produce a metal arylamide and reacting the resultant metal arylamide with water or lower aliphatic alcohol to produce an aromatic amine.
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- 6-Anilino-1,4,5-trihydroxyanthraquinones
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Blue anthraquinone dyestuffs are prepared from the reaction of 6-chloro-1,4,5-trihydroxyanthraquinone with an appropriate aniline reactant. The resultant blue dyestuffs are 6-anilino-1,4,5-trihydroxyanthraquinones which produce excellent blue dyeings on polyester fabrics, particularly polyethylene terephthalate.
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