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.

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

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Article in Molecular diversity, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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7 authors.

Lingqian WanHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, Hubei, China.

Bohao ZhangHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, Hubei, China.

Meixing ChenHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, Hubei, China.

Zhaomin JiangHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, Hubei, China.

Guodong YinHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, Hubei, China.

Shengzhou JinHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, Hubei, China. jinshengzhou@hbnu.edu.cn.

Yao ZhouHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, Hubei, China. yaozhou@hbnu.edu.cn.

Funding

Excellent Youth Innovation Team of Higher Education Institutions in Shandong Province 2024KJG030Financial supported by the National Natural Science Foundation 22301072Open Research Fund of Hubei Key Laboratory of Pollutant Analysis & Reuse Technology PA240209the Natural Science Foundation of Hubei Province 2024AFB822the Special Fund Project for Guiding Local Science and Technology Development of Hubei Province by the Central Government 2024CSA097

6 · The paper itself

Abstract

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.

Indexed as

Cycloaddition ReactionPhosphinesCatalysisCyclizationPhosphines1,3-benzothiazin-4-onesBenzo[c][1,2]dithiol-3-onesCyclization reactionIso(thio)cyanatesS-S bond cleavage

Identifiers

PMID41498888

DOI10.1007/s11030-025-11450-w

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.