Tetrahedron letters2022，Vol.975.DOI:10.1016/j.tetlet.2022.153781

Direct sulfonylamidation of unfunctionalized arenes in C-H activation manner: A simple protocol to access primary sulfonamides

Tummanapalli, Satyanarayana Bodige, Srinu Gulipalli, Kali Charan Endoori, Srinivas Medaboina, Srinivas Mallidi, Kalyani
Tetrahedron letters2022，Vol.975.DOI:10.1016/j.tetlet.2022.153781
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  • NSTL
  • Elsevier

Direct sulfonylamidation of unfunctionalized arenes in C-H activation manner: A simple protocol to access primary sulfonamides

Tummanapalli, Satyanarayana 1Bodige, Srinu 1Gulipalli, Kali Charan 1Endoori, Srinivas 1Medaboina, Srinivas 1Mallidi, Kalyani1
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作者信息

  • 1. Curia India Pvt Ltd
  • 折叠

Abstract

Among all biologically active sulfonamides, primary sulfonamides possessing terminal SO2NH2 group occupy special place due to their high zinc binding capability which has been successfully exploited for discovery of several different medicinally active primary sulfonamides. However, majority of the primary sulfonamide synthesis involve traditional method of treating ammonia with sulfonyl chloride, which in turn is typically obtained either from thiols by harsh oxidation conditions or chlorination of sulfonic acids. We herein report a simple and convenient protocol to access primary sulfonamides by direct sulfonylamidation of unfunctionalized arenes [direct C-H activation to C-SO2NH2]. Usefulness of the protocol has been further demonstrated successfully by extending the application to formal syntheses of known drugs, acetazolamide (2), methazolamide (3), ethoxzolamide (4), and a pharmacologically active benzolamide (6). (C) 2022 Elsevier Ltd. All rights reserved.

Key words

Primary sulfonamide/Dehydrogenative one step/sulfonylamidation/C-H activation/Biologically active compounds/Environment-friendly/CARBONIC-ANHYDRASE INHIBITORS/CONVENIENT PREPARATION/CRYSTAL-STRUCTURE/CHLORIDES/THIOLS/MILD

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN：0040-4039
被引量1
参考文献量67
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