Ionic Liquid-Mediated One-Pot 3‑Acylimino‑3H‑1,2-dithiole Synthesis from Thiocarboxylic Acids and Alkynylnitriles via In Situ Generation of Disulfide Intermediates
A practical and straightforward strategy for the synthesis of 3-acylimino-3H-1,2-dithiol derivatives via a metal-free annulation reaction of alkynylnitriles with thiocarboxylic acids mediated by ionic liquids [BMIM]Br has been reported. This operationally simple protocol offers an easy and rapid acc...
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Veröffentlicht in: | Journal of organic chemistry 2022-07, Vol.87 (13), p.8396-8405 |
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Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A practical and straightforward strategy for the synthesis of 3-acylimino-3H-1,2-dithiol derivatives via a metal-free annulation reaction of alkynylnitriles with thiocarboxylic acids mediated by ionic liquids [BMIM]Br has been reported. This operationally simple protocol offers an easy and rapid access to a library of dithiol derivatives in moderate to good yields. The mechanistic studies show a benzoyldithio anion addition to alkynylnitriles followed by an annulation reaction through the involvement of a disulfide moiety as the key intermediate. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.2c00301 |