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Abstract <p>NBS-Induced oxidative sulfonamidation of carbonyl terpenoids <i>l</i>-carvone and <i>l</i>-verbenone in acetonitrile was studied. The one-pot reaction of <i>l</i>-carvone with various sulfonamides affords 2,4-dimethyl-1-sulfonylimidazoline carvone derivatives in up to 74% yield and 9-bromocarvone as a by-product. In the reaction of <i>l</i>-verbenone, 2,4,4,7-tetramethyl-4<i>H</i>-benzo[<i>e</i>][1,3]oxazin-3-ium bromide salt was obtained irrespective of the taken sulfonamide, and its structure was proved by single crystal X-ray analysis. The mechanisms of both reactions were proposed.</p>

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The NBS-Induced Oxidative Sulfonamidation of Natural Monoterpene Ketones l-Carvone and l-Verbenone in Acetonitrile

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • I. A. Garagan,
  • V. S. Myasnikova,
  • M. Yu. Moskalik,
  • T. N. Borodina,
  • S. V. Zinchenko,
  • B. A. Shainyan

摘要

Abstract

NBS-Induced oxidative sulfonamidation of carbonyl terpenoids l-carvone and l-verbenone in acetonitrile was studied. The one-pot reaction of l-carvone with various sulfonamides affords 2,4-dimethyl-1-sulfonylimidazoline carvone derivatives in up to 74% yield and 9-bromocarvone as a by-product. In the reaction of l-verbenone, 2,4,4,7-tetramethyl-4H-benzo[e][1,3]oxazin-3-ium bromide salt was obtained irrespective of the taken sulfonamide, and its structure was proved by single crystal X-ray analysis. The mechanisms of both reactions were proposed.