- 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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- Functionalized GO@ZIF-90-supported sulfuric acid and its application in the catalytic synthesis of sulfonamides
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In this article, the sulfuric acid supported on the graphene oxide@ZIF-90 composite functionalized with ethylenediamine (GZAH) was synthesized and characterized with FTIR, SEM, TEM, EDS, BET, and TGA. Then, the synthesis of some sulfonamides was performed
- Ghasemi, Mohammad Hadi,Ghazviniyan, Maryam,Masnabadi, Nasrin
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- Rhodium(iii)-catalyzed sulfonamide directed ortho C-H carbenoid functionalization via metal carbene migratory insertion
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A rhodium(iii)-catalyzed sulfonamide directed ortho C-H carbenoid functionalization has been developed with good yields. This method is attractive due to its broad substrate scope, and enables derivation of diverse biologically active sulfonamide structures and late-stage modification of sulfa drugs.
- Dong, Yi,Chen, Jiajing,Xu, Heng
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supporting information
p. 2027 - 2030
(2019/02/19)
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- Rhodium-catalyzed direct C-H bond alkynylation of aryl sulfonamides with bromoalkynes
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Herein we report a novel rhodium-catalyzed ortho-mono-alkynylation of aryl sulfonamides. The reactions of N-tosylacetamides with triisopropylsilyl (TIPS)-substituted bromoalkyne are catalyzed by a [(Cp?RhCl2)2] complex without cyclization, forming ortho-(
- Hou, Hongcen,Zhao, Yongli,Pu, Shouzhi,Chen, Junmin
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supporting information
p. 2948 - 2953
(2019/03/21)
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- Iridium-Catalyzed ortho-C?H Amidation of Benzenesulfonamides with Sulfonyl Azides
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We developed herein an iridium-catalyzed direct C?H activation/ C?N bond formation reaction of benzenesulfonamides with sulfonyl azides. The amidation reaction provides a protocol for the synthesis of 2-aminobenzesulfonamides in good to excellent yields. This strategy features a wide substrate scope, tolerates a broad range of functional groups under external oxidant-free conditions and only releases molecular nitrogen as the sole by-product. Moreover, the preliminary mechanism was investigated and the proposed reaction pathway was provided. (Figure presented.).
- Hou, Hongcen,Zhao, Yongli,Sheng, Shouri,Chen, Junmin
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supporting information
p. 4393 - 4398
(2019/08/28)
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- Alkene Carboarylation through Catalyst-Free, Visible Light-Mediated Smiles Rearrangement
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A light-mediated Truce–Smiles arylative rearrangement is described that proceeds in the absence of any photocatalyst. The protocol creates two C?C bonds from simple starting materials, with the installation of an aryl ring and a difluoroacetate moiety across unactivated alkenes. The reaction proceeds via a radical mechanism, utilizing a light-mediated reduction of ethyl bromodifluoroacetate by N,N,N′,N′-tetramethylethylenediamine (TMEDA) to set up intermolecular addition to an unactivated alkene, followed by Truce–Smiles rearrangement.
- Whalley, David M.,Duong, Hung A.,Greaney, Michael F.
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supporting information
p. 1927 - 1930
(2019/01/16)
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- Catalytic activity of magnetic Fe3O4@Diatomite earth and acetic acid for the N-acylation of sulfonamides
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The Br?nsted and Lewis acidic promoted N-acylation of sulfonamides with acetic anhydride or benzoyl chloride has been achieved using glacial acetic acid and magnetic Fe3O4@Diatomite earth. Use of acetic acid as solvent omits the need for organic bases and permits the isolation of products by filtration and precipitation. Additionally, the magnetic composite Fe3O4@Diatomite acts as a conjugate proton super acid, enabling the acylation of sulfonamide compounds.
- Ghasemi, Mohammad Hadi,Kowsari, Elaheh,Hosseini, Seyed Kiumars
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supporting information
p. 387 - 391
(2016/01/12)
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- Regioselective ortho olefination of aryl sulfonamide via rhodium-catalyzed direct C-H bond activation
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Rh(III)-catalyzed ortho C-H olefination of aryl sulfonamide directed by the SO2NHAc group is reported. This oxidative coupling process is achieved highly efficiently and selectively with a broad substrate scope. The reactions of N-tosylacetamid
- Xie, Weijia,Yang, Jie,Wang, Baiquan,Li, Bin
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p. 8278 - 8287
(2015/03/18)
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- N -acyl DBN tetraphenylborate salts as N -acylating agents
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Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been synthesized from 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) and the corresponding acyl chloride in the presence of sodium tetraphenylborate. The salts have been shown to be effective N-acylating agents, reacting with primary amines, secondary amines, and sulfonamides to form the corresponding N-acylated products in good yields. The DBN hydrotetraphenylborate byproduct can be conveniently removed by filtration, providing pure N-acylated products without the need for further purification. The N-acyl DBN tetraphenylborate salts are attractive alternatives to acyl halides as they can be stored in air without decomposition, avoid the production of free acid during acylation reactions, and can be used under more forcing thermal conditions.
- Taylor, James E.,Jones, Matthew D.,Williams, Jonathan M. J.,Bull, Steven D.
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experimental part
p. 2808 - 2818
(2012/04/23)
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- TiCl4-promoted direct N-acylation of sulfonamide with carboxylic ester
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Several Lewis acids were investigated as promoters in the intermolecular or intramolecular direct N-acylation reaction of sulfonamides using carboxylic ester as an acylating agent. TiCl4 was found to possess the highest activity and enhanced efficiently sulfonamide to form N-acylsulfonamides under optimized conditions. This method provides a novel approach to make N-acylsulfonamides from ester via an easy work-up procedure.
- Fu, Shaomin,Lian, Xiaoyan,Ma, Tongmei,Chen, Wenhua,Zheng, Meifang,Zeng, Wei
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supporting information; experimental part
p. 5834 - 5837
(2010/11/04)
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- HCIO4-SiO2 and NaHSO4-SiO2: Two efficient heterogeneous catalysts for synthesis of N-Acylsulfonamides under solvent-free conditions
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A simple and efficient synthesis of N-acylsulfonamides has been accomplished by the reaction of sulfonamides with anhydrides under solvent-free conditions in the presence of HClO4-SiO2 or NaHSO4-SiO2.copy;2009. Bentham Science Publis
- Liqiang, Wu,Chunguang, Yang,Chong, Zhang,Liming, Yang
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experimental part
p. 234 - 236
(2010/04/23)
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- Fe-exchanged montmorillonite K10 - The first heterogeneous catalyst for acylation of sulfonamides with carboxylic acid anhydrides
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Fe-exchanged montmorillonite K10 catalyzes a highly efficient reaction between sterically and electronically diverse sulfonamides and carboxylic acid anhydrides to furnish N-acylsulfonamides in excellent yield and high selectivity. The catalyst can also be reused several times.
- Singh, Devendrapratap U.,Singh, Pankajkumar R.,Samant, Shriniwas D.
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p. 4805 - 4807
(2007/10/03)
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- Cathodic Reductions of Acid Azides. Electrolytic Studies on Vinyl Acides, VIII
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The cathodic reduction of the O=C-N3-system in aprotic solvent in the presence of anhydrides proves to be a convenient way to triacylammonia derivatives.Using the complexation of Li(+) ions with the acid azide this synthetic methods can start from non-dangerous acid halides.The complex formation constant has been estimated and the chemical stability of N,N-diacylamides produced has been investigated.Mechanistic details about the role of Li(+)-ions in these electrolyses are given.Further reduction of the triacylammonia derivatives at more negative potentials results in protected aldehydic functions, i.e. 1-acyloxy-1-diacylaminomethanes, in good yields. - Keywords: Acid azides; N,N-Diacylamides; 1-Acyloxy-1-diacetyl-aminomethanes; Lithiumion-azide complexes; Cathodic reduction
- Knittel, Dierk
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p. 379 - 388
(2007/10/02)
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- Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines
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A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.
- Davis, Franklin A.,Lamendola, Joseph,Nadir, Upender,Kluger, Edward W.,Sedergran, Thomas C.,et al.
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p. 2000 - 2005
(2007/10/02)
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