Literature DB >> 26771228

One-Step Synthesis of Sulfonamides from N-Tosylhydrazones.

Andy S Tsai1, John M Curto1, Benjamin N Rocke1, Anne-Marie R Dechert-Schmitt1, Gajendrasingh K Ingle1, Vincent Mascitti1.   

Abstract

The first described reaction between N-tosylhydrazone and SO2 is reported to provide alkyl sulfonamides in the presence of various amines. In this procedurally simple method, hydrazones of both unsaturated aldehydes and ketones proceed in moderate to excellent yields. Primary and secondary aliphatic amines are accommodated in this reaction, which provides a novel route to sulfonamides.

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Year:  2016        PMID: 26771228     DOI: 10.1021/acs.orglett.5b03545

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent.

Authors:  Hang T Dang; Vu T Nguyen; Viet D Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  Org Biomol Chem       Date:  2018-05-15       Impact factor: 3.876

2.  Iodine-catalyzed sulfonylation of sulfonyl hydrazides with tert-amines: a green and efficient protocol for the synthesis of sulfonamides.

Authors:  Jinyang Chen; Xiaoran Han; Lan Mei; Jinchuan Liu; Kui Du; Tuanwu Cao; Qiang Li
Journal:  RSC Adv       Date:  2019-10-02       Impact factor: 4.036

3.  Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides.

Authors:  Vu T Nguyen; Graham C Haug; Viet D Nguyen; Ngan T H Vuong; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2021-04-13       Impact factor: 9.825

4.  One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.

Authors:  Alyn T Davies; John M Curto; Scott W Bagley; Michael C Willis
Journal:  Chem Sci       Date:  2016-10-11       Impact factor: 9.825

5.  Rapid Synthesis of N-Tosylhydrazones under Solvent-Free Conditions and Their Potential Application Against Human Triple-Negative Breast Cancer.

Authors:  Zengyang Xie; Yuying Song; Lujia Xu; Yukun Guo; Min Zhang; Limei Li; Kai Chen; Xue Liu
Journal:  ChemistryOpen       Date:  2018-11-21       Impact factor: 2.911

6.  Sustainable Synthesis of a Potent and Selective 5-HT7 Receptor Antagonist Using a Mechanochemical Approach.

Authors:  Vittorio Canale; Valeria Frisi; Xavier Bantreil; Frédéric Lamaty; Paweł Zajdel
Journal:  J Org Chem       Date:  2020-08-11       Impact factor: 4.354

7.  An Efficient Method for the Preparation of Sulfonamides from Sodium Sulfinates and Amines.

Authors:  Haiying Tian; Ruiyan Li; Fang Guo; Xiuling Chen
Journal:  ChemistryOpen       Date:  2022-08       Impact factor: 2.630

  7 in total

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