- Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
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We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
- Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
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supporting information
p. 9419 - 9424
(2021/11/30)
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- Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines
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The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).
- Ojha, Subhadra,Panda, Niranjan
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p. 561 - 571
(2019/12/24)
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- New allyldithiocarbimate salts: Synthesis, structure and antifungal activity
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Fifteen new allyldithiocarbimates were prepared from different allylic bromides and various potassium dithiocarbimates, yielding (Z)-2-(methoxycarbonyl)-3-(X-nitrophenyl)allyl-(N-R-sulfonyl)dithiocarbimates (where X = 2, 3 and 4; R = phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl and 4-iodophenyl). These anions were isolated as tetraphenylphosphonium salts and characterized by HRMS, infrared, 1H and 13C NMR spectroscopies. Molecular electrostatic potentials were used to evaluate intermolecular interactions present in the new substances and to explain variations observed on their melting points. Single crystal X-ray diffraction experiments confirmed the Z stereochemistry of the allyldithiocarbimate anions. C–H?O, C–H?N, C–H?S and C–H?π intermolecular interactions in the solid state were studied by X-ray diffraction and Hirshfeld surface analyses. The new compounds inhibited the mycelial growth of various fungi species responsible for severe plant diseases. The allylithiocarbimates were especially active against Botrytis cinerea, with IC50 values as low as 20 μM, being more effective than the active principals of the commercial fungicides Ziram and Mancozeb.
- Albuini-Oliveira, Nathália M.,Alvarez, Natalia,Ellena, Javier,Guilardi, Silvana,Lima, Marcelo S.,Rubinger, Mayura M. M.,Souza, Rafael A. C.,Tavares, Eder C.,Vidigal, Antonio E. C.,Zacchi, Carlos H. C.,Zambolim, Laercio
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- Sulfonamide compound and synthesis method and application thereof
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The invention discloses a synthesis method of a sulfonamide compound represented in a formula (2). According to the method, diazonium salt is used as a reaction raw material, and under the action of an inorganic nitrogen reagent, an inorganic sulfur dioxide reagent, an additive and a phosphine reagent, the diazonium salt is reacted in a solvent at 60-100 DEG C to obtain various sulfonamide compounds. According to the method inorganic salt is used as a nitrogen atom source and a sulfur dioxide source under a metal-free catalytic condition to construct the sulfonamide compound through one step,thereby avoiding the conventional multi-step synthesis of sulfonamide by condensing unstable acid chloride and amine; and the developed sulfonamide synthesis method can be further applied to the synthesis of the arthritis drug celecoxib and the psychotropic drug sulpiride.
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Paragraph 0070-0073
(2019/04/02)
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- Metal-free construction of primary sulfonamides through three diverse salts
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In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with -SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.
- Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
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supporting information
p. 5469 - 5473
(2019/01/03)
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- Bis(diaryliodonium) perfluorosulfonimide zwitterions as potential photo acid generators
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Three examples of bis(diaryliodonium) perfluorosulfonimide (BDI-PFSI) zwitterions have been prepared as a potential new class of ionic photo-acid generators for chemically amplified photoresist formulations.
- Mei, Hua,Desmarteau, Darryl D.
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- 3,5-Disubstituted-thiazolidine-2,4-dione analogs as anticancer agents: Design, synthesis and biological characterization
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A series of 2,5-disubstituted-thiazolidine-2,4-dione analogs based on the newly identified lead 1, a potential anticancer agent via the inhibition of the Raf/MEK/extracellular signal regulated kinase (ERK) and phosphatidylinositol 3-kinase (PI3K)/Akt signaling cascades, were synthesized and biologically characterized. A new lead structure, 15, was identified to have improved anti-proliferative activities in U937 cells, to induce apoptosis in U937, M12 and DU145 cancer cells, and to arrest U937 cells at the S-phase. Furthermore, Western blot analysis demonstrated a correlation of the anti-proliferative activity and blockade of the Raf/MEK/ERK and PI3K/Akt signaling pathways. Collectively, these results strongly encourage further optimization of 15 as a new lead with multi-target properties to develop more potent compounds as anticancer agents.
- Liu, Kai,Rao, Wei,Parikh, Hardik,Li, Qianbin,Guo, Tai L.,Grant, Steven,Kellogg, Glen E.,Zhang, Shijun
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experimental part
p. 125 - 137
(2012/03/08)
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- Syntheses, crystal structure, spectroscopic characterization and antifungal activity of novel dibutylbis(N-R-sulfonyldithiocarbimato)stannate(IV) complexes
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Five new complexes of the general formula: (Ph4P) 2[Sn(Bu)2(RSO2NCS2)2], where Ph4P = tetraphenylphosphonium cation, Bu = n-butyl and R = C6H5 (1), 4-FCsub
- Dias, Letícia C.,Rubinger, Mayura M.M.,Barolli, Jo?o P.,Ardisson, José D.,Mendes, Isolda C.,De Lima, Geraldo M.,Zambolim, Laércio,Oliveira, Marcelo R.L.
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- PYRAZINE DERIVATIVES AND USE AS PI3K INHIBITORS
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The present invention is related to pyrazine derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.
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Page/Page column 41-42
(2008/06/13)
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- NOVEL HETEROCYCLIC AMIDE DERIVATIVES HAVING DIHYDROOROTATE DEHYDROGENASE INHIBITING ACTIVITY
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Novel heterocyclic amide derivatives having pharmacological effects, that is, compounds represented by the general formula (1) or salts thereof: (1) wherein X1-X2 is S-CH2 or the like; R1 is alkyl or the like; p is 0 to 7; R2 is hydrogen, alkyl, or the like; R3 is hydrogen, alkyl, or the like; Y1-Y2 is CH=CH or the like; R4 is halogeno, alkyl, or the like; q is 0 to 4; and R5 is halogeno, hydrogen, alkyl, or the like.
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Page/Page column 69
(2010/10/20)
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- New phenylpyridylpiperazine compounds
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A compound selected from those of formula (I): [image] wherein: X represents a C(O) or SO2 group, R1 represents an aryl group or a group NR3R4 wherein R3 and R4 are as defined in the description, R2 represents an alkyl, (C3-C8)cycloalkyl or (C3-C8)cycloalkyl-(C1-C6)alkyl group, its isomers, and addition salts thereof, and medicinal products containing the same which are useful in treating conditions treatable by antagonists of type H3 central histamine receptors.
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Page/Page column 10
(2008/06/13)
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- Novel thiocarbamic acid derivatives and the pharmaceutical compositions containing the same
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The present invention relates to an antagonist against vanilloid receptor and the pharmaceutical compositions containing the same. As diseases associated with the activity of vanilloid receptor, pain, acute pain, chronic pain, neuropathic pain, post-opera
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- Novel thiourea derivatives and the pharmaceutical compositions containing the same
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The present invention relates to novel thiourca derivatives as a modulator for vanilloid receptor (VR) and the phar- maceutical compositions containing the same. As diseases associated with the activity of vanilloid receptor, pain acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neuropathies, nerve injury, diabetic neuropathy, neurodegeneration, neurotic skin disorder, stroke, urinary bladder hypersensitiveness, irritable bowel syndrome, a respiratory disorder such as asthma or chronic obstructive pulmonary disease, irritation of skin, eye or mucous membrane, fervescence, stomach-duodenal ulcer, inflam- matory bowel disease and inflammatory diseases can be enumerated. The present invention provides a pharmaceutical composition for prevention or treatment of these diseases.
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- Preparation of nitrogen-containing 15-membered triolefinic macrocycles: (E,E,E)-1,6,11-tris(arylsulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-trienes
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Three routes to (E,E,E)-1,6,11-tris(arylsulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-trienes are described. Optimization of the preparation of key intermediates has opened the way to efficient synthesis of a broad variety of 15-membered, nitrogen-containing triolefinic macrocycles.
- Cerezo, Silvia,Cortès, Jordi,Galvan, David,Lago, Elena,Marchi, Caroline,Molins, Elies,Moreno-Ma?as, Marcial,Pleixats, Roser,Torrejón, Javier,Vallribera, Adelina
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p. 329 - 337
(2007/10/03)
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- Application of the sulfonamide functional groups as an anchor for solid phase organic synthesis (SPOS)
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Sulfonyl chlorides have been found to readily couple to an amino functionalized resin. The resulting sulfonamide anchoring group is stable to a variety of reactions commonly used in SPOS. Acid induced cleavage is facile, affording functionalized sulfonamides in high yields.
- Beaver,Siegmund,Spear
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p. 1145 - 1148
(2007/10/03)
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