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

YILMAZ E. S., ZORA M.

SYNTHETIC COMMUNICATIONS, vol.51, no.5, pp.709-719, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 51 Issue: 5
  • Publication Date: 2021
  • Doi Number: 10.1080/00397911.2020.1850795
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, EMBASE
  • Page Numbers: pp.709-719
  • Keywords: 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: Yes

Abstract

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.