Journal
SYNTHETIC COMMUNICATIONS
Volume 51, Issue 5, Pages 709-719Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2020.1850795
Keywords
Alkynes; cyclization; beta-enaminones; Lawesson's reagent; N-propargylic N-(2,4-pentadiynyl) beta-enaminothiones; 1,4-thiazepines
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Funding
- Scientific and Technological Research Council of Turkey [TUBITAK] [114Z811]
- Research Fund of Middle East Technical University [METU] [GAP-103-2018-2770]
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This study reports a novel method for the synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines from N-(2,4-pentadiynyl) beta-enaminones. The method involves thionation and cyclization reactions, demonstrating broad functional group tolerance and potentially providing quick access to a library of functionalized 1,4-thiazepines in pharmaceutical chemistry.
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. [GRAPHICS] .
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