Synthesis of 1,4-Thiazepines

Date

2018-08-03

Author

Kelgokmen, Yılmaz
Zora, Metin

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An efficient, general, and unprecedented methodology for the synthesis of 2-methylene-2,3-dihydro-1,4-thiazepines from N-propargylic beta-enaminones is described. Initially, N-propargylic beta-enaminones were thionated with Lawesson's reagent in good to high yields, and then the resulting N-propargylic beta-enaminothiones were subjected to electrophilic cyclization. When treated with zinc chloride in refluxing chloroform, Npropargylic beta-enaminothiones underwent electrophilic cyclization to yield 2-methylene-2,3-dihydro-1,4-thiazepines in good to high yields. A general trend was observed for all N-propargylic beta-enaminothiones, and the cyclization proceeded with high efficiency and large functional group tolerance. This process is also applicable to the cyclization of internal alkyne-tethered N-propargylic beta-enaminothiones. This operationally simple and facile method may represent a very rapid entry to a library of functionalized 1,4-thiazepines in the area of pharmaceuticals.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/35156

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/acs.joc.8b01029

Collections

Department of Chemistry, Article

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Citation Formats

Y. Kelgokmen and M. Zora, “Synthesis of 1,4-Thiazepines,” JOURNAL OF ORGANIC CHEMISTRY, pp. 8376–8389, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35156.