A facile one-pot synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines

Date

2020-11-01

Author

Yılmaz, Elif Serel
Zora, Metin

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An unprecedented method for the synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines from N-(2,4-pentadiynyl) beta-enaminones is reported. Upon treatment with Lawesson's reagent, N-(2,4-pentadiynyl) beta-enaminones were thionated to furnish N-(2,4-pentadiynyl) beta-enaminothiones, which immediately underwent 7-exo-dig cyclization to generate 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines in one-pot. A general trend was observed for various N-(2,4-pentadiynyl) beta-enaminones and cyclization proceeded with broad functional group tolerance. This operationally easy method may provide quick access to a library of functionalized 1,4-thiazepines in the field of pharmaceutical chemistry.

Subject Keywords

Organic Chemistry, alkynes, cyclization, β-enaminones, Lawesson’s reagent, N-propargylic N-(2,4-pentadiynyl) β-enaminothiones, 1,4-thiazepines

URI

https://hdl.handle.net/11511/69318

Journal

SYNTHETIC COMMUNICATIONS

DOI

https://doi.org/10.1080/00397911.2020.1850795

Collections

Department of Chemistry, Article

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Citation Formats

E. S. Yılmaz and M. Zora, “A facile one-pot synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines,” SYNTHETIC COMMUNICATIONS, 2020, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/69318.