SYNTHETIC COMMUNICATIONS, vol.51, no.5, pp.709-719, 2021 (SCI-Expanded)
Article / Article
Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, EMBASE
Alkynes, cyclization, beta-enaminones, Lawesson's reagent, N-propargylic N-(2,4-pentadiynyl) beta-enaminothiones, 1,4-thiazepines, PROPARGYLIC BETA-ENAMINONES, CATALYZED SYNTHESIS, IDENTIFICATION, DERIVATIVES, TERBINAFINE, 1,5-BENZOTHIAZEPINE, CYCLIZATION, QUETIAPINE, INHIBITOR, DILTIAZEM
Middle East Technical University Affiliated:
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.