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, cilt.51, sa.5, ss.709-719, 2021 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 51 Konu: 5
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1080/00397911.2020.1850795
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Sayfa Sayıları: ss.709-719

Özet

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.