Reactions of Thioamides with Iminoiodinanes: An Approach toward 1,2-Thiazines, Thiophenes, and Sulfonylisothiazolines
Transition metal-catalyzed and noncatalytic reactions of acrylic thioamides with <i>N</i>-sulfonyliminoiodinanes enabling the selective synthesis under mild conditions of a series of fully decorated S- and N,S-containing heterocycles are described. Fine-tuning of the thioamide structure allows selective preparation in good yields of ortho-fused thiophenes, 1,2-thiazines, and spiro-fused isothiazolines. A one-pot thermally induced rearrangement of sulfonylisothiazolines was discovered as a complementary route to thiophenes.
Authors
- Tetyana Beryozkina (ORCID: https://orcid.org/0000-0002-9917-6748)
- Павел А. Слепухин (ORCID: https://orcid.org/0000-0001-8132-9905)
- Vladimir G. Ilkin (ORCID: https://orcid.org/0000-0003-4819-8944)
- Wim Dehaen (ORCID: https://orcid.org/0000-0002-9597-0629)
- Vasiliy А. Bakulev (ORCID: https://orcid.org/0000-0002-3312-7783)
- P. S. Silaichev (ORCID: https://orcid.org/0000-0002-2840-6809)
- Ilya D. Gridnev (ORCID: https://orcid.org/0000-0002-6711-9036)
- Михаил С. Новиков (ORCID: https://orcid.org/0000-0001-5106-4723)
Institutions
- Perm State University (RU)
- Ural Federal University (RU)
- St Petersburg University (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
- Institute of Organic Synthesis (RU)
- Ural Branch of the Russian Academy of Sciences (RU)
- KU Leuven (BE)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-06
- DOI
- https://doi.org/10.1021/acs.joc.4c02623
- Citations
- 3
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- Russian Science Foundation