- Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides
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The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3and AlI3display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, sec
- Sang, Dayong,Dong, Bingqian,Liu, Yunfeng,Tian, Juan
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p. 3586 - 3595
(2022/02/25)
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- 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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- Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl- O-(tert-butyl)hydroxylamine, t-BuONSO
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Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, t-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process.
- Davies, Thomas Q.,Hall, Adrian,Skolc, David,Tilby, Michael J.,Willis, Michael C.
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supporting information
p. 9495 - 9499
(2020/12/21)
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- One-pot aerobic oxidative sulfonamidation of aromatic thiols with ammonia by a dual-functional β-MnO2 nanocatalyst
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High-surface-area β-MnO2 (β-MnO2-HS) nanoparticles could act as effective heterogeneous catalysts for the one-pot oxidative sulfonamidation of various aromatic and heteroaromatic thiols to the corresponding sulfonamides using molecular oxygen (O2) and ammonia (NH3) as respective oxygen and nitrogen sources, without the need for any additives.
- Hayashi, Eri,Yamaguchi, Yui,Kita, Yusuke,Kamata, Keigo,Hara, Michikazu
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supporting information
p. 2095 - 2098
(2020/02/26)
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- Highly Chemoselective NH- and O-Transfer to Thiols Using Hypervalent Iodine Reagents: Synthesis of Sulfonimidates and Sulfonamides
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Aryl thiols can be selectively converted to sulfonimidates or sulfonamides with three new S-X connections being made selectively in one pot. Using hypervalent iodine reagents in the presence of ammonium carbamate, NH- and O-groups are transferred under mild and practical conditions. Reducing the loading of ammonium carbamate changed the product distribution, converting the sulfonimidate to the sulfonamide. Studies into the possible intermediate species are presented, suggesting that multiple pathways may be possible via sulfinate esters, or related intermediates, with each species forming the same products.
- Tota, Arianna,St John-Campbell, Sahra,Briggs, Edward L.,Estévez, Gala Ogalla,Afonso, Michelle,Degennaro, Leonardo,Luisi, Renzo,Bull, James A.
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supporting information
p. 2599 - 2602
(2018/05/22)
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- Cu(II)-catalyzed decarboxylation/elimination of N-arylsulfonyl amino acids to primary aryl sulfonamides
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A novel protocol for CuO-catalyzed decarboxylation/elimination of N-arylsulfonyl amino acids was developed. It is the first example of using an accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl sulfonamides via oxidative decarboxylation/elimination reactions. The present protocol shows excellent functional group tolerance and provides an efficient method for the synthesis of primary aryl sulfonamides in excellent yields.
- Zhou, Liandi,Li, Xiaokang,Liu, Wei,Zhao, Yongli,Chen, Junmin
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p. 1299 - 1306
(2016/08/16)
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- Cu-catalyzed aerobic oxidative three-component coupling route to N -sulfonyl amidines via an ynamine intermediate
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Cu-catalyzed aerobic oxidative three-component coupling of a terminal alkyne, secondary amine, and sulfonamide enables efficient synthesis of amidines. The use of Cu(OTf)2 (5 mol %) produces amidines selectively without Glaser-Hay alkyne homocoupling products. Preliminary studies suggest that the reaction pathway involves initial oxidative coupling of the terminal alkyne with the secondary amine, followed by hydroamidation of the ynamine intermediate with the sulfonamide.
- Kim, Jinho,Stahl, Shannon S.
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p. 2448 - 2454
(2015/04/14)
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- In situ formation of vilsmeier reagents mediated by oxalyl chloride: A tool for the selective synthesis of N-sulfonylformamidines
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N-Sulfonylformamidines were produced from sulfonamides or N-acylated sulfonamides using Vilsmeier reagent obtained in situ from N,N-disubstituted formamides and oxalyl chloride. Optically active substrates did not racemize during the process. The efficient and mild cleavage of N-sulfonylformamidines can be achieved with hydrazine hydrate in ethanol. The entire procedure constitutes a simple method for protecting, and deprotecting, the sulfonamide moiety. A straightforward and efficient synthesis for N-sulfonylformamidines by employment of various Vilsmeier reagents generated in situ is described. The reactions proceed under mild reaction conditions and tolerate several sensitive functional groups. Copyright
- Gazvoda, Martin,Kocevar, Marijan,Polanc, Slovenko
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p. 5381 - 5386
(2013/09/02)
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- 1,4-QUINONES AND THEIR SULFUR ANALOGUES USEFUL AS LIGANDS OF N-ACETYLTRANSFERASES
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The invention provides 1,4-quinones, 1,4-naphthoquinones and their sulphur analogues as inhibitors of hNAT1, an enzyme which is both a diagnostic marker and drug target for breast cancer. Some of the compounds of the invention are also chromogenic in the
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Page/Page column 47
(2011/06/11)
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- HEPATITIS C VIRUS INHIBITORS
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Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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- Hepatitis C Virus Inhibitors
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Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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- MACROCYCLIC PEPTIDES AS HEPATITIS C VIRUS INHIBITORS
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Macrocyclic peptides having the general formula (I): are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 64
(2008/12/05)
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- Hepatitis C Virus Inhibitors
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Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 30
(2008/12/05)
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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 43
(2008/06/13)
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- Hepatitis C virus inhibitors
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The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which inhibit the function of the NS3 protease (also referred to herein as “serine protease”) encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS3 protease.
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Page/Page column 32
(2008/06/13)
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- Acyl sulfonamide anti-proliferatives. Part 2: Activity of heterocyclic sulfonamide derivatives
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The anti-proliferative activity of acylated heterocyclic sulfonamides is described in Vascular Endothelial Growth Factor-dependent Human Umbilical Vascular Endothelial Cells (VEGF-HUVEC) and in HCT116 tumor cells in a soft agar diffusion assay.
- Mader, Mary M.,Shih, Chuan,Considine, Eileen,De Dios, Alfonso,Grossman, Cora Sue,Hipskind, Philip A.,Lin, Ho-Shen,Lobb, Karen L.,Lopez, Beatriz,Lopez, Jose E.,Cabrejas, Luisa M. Martin,Richett, Michael E.,White, Wesley T.,Cheung, Yiu-Yin,Huang, Zhongping,Reilly, John E.,Dinn, Sean R.
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p. 617 - 620
(2007/10/03)
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- Inhibitors of β-lactamase
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The intention relates to bacterial antibiotic resistance and, in particular, to compositions and methods for overcoming bacterial antibiotic resistance. The invention provides novel β-lactamase inhibitors, which are structurally unrelated to the natural p
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- Scandium triflate as an efficient and recyclable catalyst for the deprotection of tert-butyl aryl sulfonamides
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A mild and efficient method for deprotection of tert-butyl sulfonamide groups utilizing Sc(OTf)3 as deprotecting reagent has been developed. A variety of tert-butyl aryl sulfonamides used under these conditions gave the corresponding primary sulfonamides in high yields. The Lewis acid catalyst could be fully recovered and reused with maintained activity after the reactions. Copyright Taylor & Francis, Inc.
- Mahalingam,Wu, Xiongyu,Wan, Yiqian,Alterman, Mathias
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p. 417 - 425
(2007/10/03)
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- Novel inhibitors of beta-lactamase
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The intention relates to bacterial antibiotic resistance and, in particular, to compositions and methods for overcoming bacterial antibiotic resistance. The invention provides novel β-lactamase inhibitors, which are structurally unrelated to the natural p
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- Novel Inhibitors of beta-lactamase
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The invention relates to bacterial antibiotic resistance and, in particular, to compositions and methods for overcoming bacterial antibiotic resistance. The invention provides novel β-lactamase inhibitors, which are structurally unrelated to the natural p
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- HETEROCYCLIC COMPOUND DERIVATIVES AND MEDICINES
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The present invention provides a compound which is useful as a PGI2 receptor agonist, and a pharmaceutical composition. The present invention is directed to a pharmaceutical composition comprising a compound represented by the following formula [1]: (R1 and R2 are the same or different and each represents optionally substituted aryl, Y represents N or CH, Z represents N or CH, A represents NH, NR5, O, S, or ethylene, R5 represents alkyl, D represents alkylene or alkenylene, E represents phenylene or single bond, G represents O, S, or CH2, R3 and R4 are the same or different and each represents hydrogen or alkyl, Q represents carboxy, alkoxycarbonyl, tetrazolyl, carbamoyl, or N-(alkylsulfonyl)carbamoyl), or a pharmaceutically acceptable salt thereof as an active ingredient.
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- Hepatitis C virus inhibitors
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The present invention relates to tripeptide compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. In particular, the present invention provides novel tripeptide analogs, pharmaceutical compositions containing such analogs and methods for using these analogs in the treatment of HCV infection.
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- Synthesis and properties of N-(2,2,2-trichloroethyl)-2- thiophenesulfonamides
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Chlorination of 2-thiophenesulfonamide gave unstable N,N-dichloro-2- thiophenesulfonamide which was brought into reactions with 1,2-polyhaloethenes. The condensation of 2-thiophenesulfonamide with trichloroacetaldehyde afforded N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide which reacted with benzene, toluene, 2-chlorothiophene, and phenol to form the corresponding N-(1-aryl-2,2,2-trichloroethyl)-2-thiophenesulfonamides. Under more severe conditions, the latter were converted into 1,1-diaryl-2,2,2-trichloroethanes. The reaction of N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide with substituted arenes, including phenol, was regioselective: only the corresponding para-substituted products were obtained. Hydrolysis of N-[2,2,2-trichloro-1-(4- tolyl)ethyl]-2-thiophenesulfonamide yielded N-(2-thienylsulfonyl)-2-(4-tolyl) glycine.
- Aizina,Rozentsveig,Levkovskaya,Mirskova
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p. 1334 - 1337
(2007/10/03)
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- HETEROCYCLICSULFONAMIDE HEPATITIS C VIRUS INHIBITORS
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The present invention relates to tripeptide compounds, compositionscontaining such compounds and methods for using such compounds for the treatment of heptitis C virus (HCV) infection. In particular, the present invention provides novel tripeptide analogs, pharmaceutical compositionscontaining such analogs and methods for using these analogs in the treatment of HCV infection.
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- Boron trichloride as an efficient and selective agent for deprotection of tert-butyl aryl sulfonamides
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A fast, mild and selective method for deprotection of tert-butyl aryl sulfonamides utilizing BCl3 as deprotection reagent has been developed. A variety of tert-butyl aryl sulfonamides used under these conditions gave the corresponding primary sulfonamides in high yields. The method does not cleave methoxy groups and prevents incorporation of tert-butyl groups onto electron-rich aromatic rings.
- Wan, Yiqian,Wu, Xiongyu,Kannan, Mahalingam A.,Alterman, Mathias
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p. 4523 - 4525
(2007/10/03)
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- Sulfonamidomethyl phosphonate inhibitors of beta-lactamase
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The intention relates to bacterial antibiotic resistance and, in particular, to compositions and methods for overcoming bacterial antibiotic resistance. The invention provides novel β-lactamase inhibitors, which are structurally unrelated to the natural p
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- Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment
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Compounds of formula I: as well as pharmaceutically acceptable salts, hydrates and esters thereof, are disclosed. The compounds are useful for treating or preventing prostaglandin mediated diseases. Pharmaceutical compositions containing such compounds and methods of treatment are also included.
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- Antitumor compositions and methods of treatment
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This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
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- A Novel One-Pot Conversion of Methyl Sulfones to Sulfonamides
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A one-pot synthesis of sulfonamides from methyl sulfones has been developed.Treatment of methyl sulfones with base and trialkylboranes gave the corresponding rearranged sulfinic acid salts which were converted to sulfonamides during oxidative-amination workup.
- Huang, Horng-Chih,Reinhard, Emily J.,Reitz, David B.
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p. 7201 - 7204
(2007/10/02)
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- Unconventional Regiospecific Syntheses of Aromatic Carbonamides and Thiocarbonamides by Means of Tin-Mediated Friedel-Crafts Reactions
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Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group.Thus, unconventionally substituted aromatic carbonamides can be obtained.The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings.The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22.One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29.Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28.From the reactions of 1 with ethoxycarbonyl isocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible.The scope, limitations, and mechanism of these electrophilic substitutions are outlined.
- Arnswald, Martin,Neumann, Wilhelm P.
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p. 7022 - 7028
(2007/10/02)
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- SODIUM BOROHYDRIDE REDUCTION OF AROMATIC SULFONYL AZIDES IN THE PRESENCE OR ABSENCE OF TELLURIUM
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Some aromatic sulfonyl azides have been reduced, in various solvents, with sodium borohydride, in the presence or absence of Te element to the corresponding sulfonamides.Other functionals groups like the imino group may also be reduced.
- Obafemi, Craig. A.,Onigbinde, Adebayo O.
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- Preparation and Utility of Dianions from N-tert-Butylthiophene-2-sulfonamide
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Metalation of N-tert-butylthiophene-2-sulfonamide with n-butyllithium occurs competitively at the 3- and 5-position of the thiophene ring.Equilibration of the initial mixture of carbanions or metalation with lithiumdiisopropylamide allows selective formation of the N,5-dilithiothiophenesulfonamide 7.This dianion is useful for the preparation of a number of 5-substituted thiophene-2-sulfonamides.
- Graham, Samuel L.,Scholz, Thomas H.
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p. 4260 - 4263
(2007/10/02)
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- THE REACTIONS OF SOME THIOPHENE SULFONYL DERIVATVES
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Thiophene-2-sulfonyl chloride has been allowed to react with 7 amines, hydrazine and sodium azide.The hydrazide was converted into 21 hydrazones.The azide reacts with cyclohexene, norbornene and triphenylphosphine.The sulfonyl chloride with chlorosulfonic acid gave a mixture of the 2,4- and 2,5-bis-sulfonyl chlorides (2:1).These were not separated by conversion to amides, azides, hydrazides, or hydrazones. 2-Carboxythiophene with chlorosulfonic acid gave a mixture of the 4- and 5-sulfonyl chlorides (9:1), conversion to amides and recrystallization gave the 4-sulfonamides.Chlorosulfonation of 2-carboxamido- and 2-N,N-dimethylcarboxamidothiophene gave the 4-sulfonyl chlorides, characterized as amides, hydrazides and 18 hydrazones.Some N-arylthiophenesulfonamides were condensed with trichloromethylsulfonyl chloride.The i.r., n.m.r. and mass spectra of the various thiophenesulphonyl derivatives are discussed.
- Cremlyn, Richard J.,Goulding, Kenneth H.,Swinbourne, Frederick J.,Yung, Kin-Man
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p. 111 - 120
(2007/10/02)
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- STUDIES IN THE HETEROCYCLIC COMPOUNDS: I. SOME 2-THIOPHENESULFONYL DERIVATIVES
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2-Thiophenesulfonyl chloride, prepared by treating thiophene with chlorosulfonic acid, has been condensed with nucleophilic reagents; ammonia, cyclohexylamine, N-methylaniline and sodium azide to afford the sulfonamide, N-cyclohexyl sulfonamide, N,N-methylphenyl sulfonamide and the sulfonyl azide respectively.The sulfonyl azide has been reacted with triphenylphosphine, tri-n-butylphosphine, norbonene and cyclohexene.The ir end nmr spectral characteristics of the products are very briefly discussed.
- Obafemi, Craig A.
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p. 197 - 200
(2007/10/02)
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