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<p>Presented herein is a fundamentally new organophosphine-mediated annulation paradigm that converts benzo[c][1,2]dithiol-3-ones and iso(thio)cyanates into pharmacologically relevant 1,3-benzothiazin-4-one architectures through an unconventional S to C-N atom exchange process. Distinct from conventional cyclization approaches, this metal-free strategy offers exceptional advantages including: broad substrate scope (45 examples, up to 96% yield), simple operation (ambient temperature, open flask), mild reaction conditions and exceptional utility in late-stage functionalization of bioactive molecules. Comprehensive mechanistic analysis uncovered a phosphine-mediated S-S bond activation followed by formal [4 + 2] cyclization.</p>

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Organophosphine-mediated formal [4 + 2] cycloadditions of benzo[c][1,2]dithiol-3-ones and iso(thio)cyanates via S to C-N skeletal editing strategy

  • 期刊论文

  • 发表日期：

    2026年1月7日

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  • Lingqian Wan,
  • Bohao Zhang,
  • Meixing Chen,
  • Zhaomin Jiang,
  • Guodong Yin,
  • Shengzhou Jin,
  • Yao Zhou

摘要

Presented herein is a fundamentally new organophosphine-mediated annulation paradigm that converts benzo[c][1,2]dithiol-3-ones and iso(thio)cyanates into pharmacologically relevant 1,3-benzothiazin-4-one architectures through an unconventional S to C-N atom exchange process. Distinct from conventional cyclization approaches, this metal-free strategy offers exceptional advantages including: broad substrate scope (45 examples, up to 96% yield), simple operation (ambient temperature, open flask), mild reaction conditions and exceptional utility in late-stage functionalization of bioactive molecules. Comprehensive mechanistic analysis uncovered a phosphine-mediated S-S bond activation followed by formal [4 + 2] cyclization.