A facile synthesis of 6-[(4-nitrophenyl)thio]-substituted 2-methylene-2,3-dihydro-1,4-oxazepines from N-propargylic beta-enaminones

KELGÖKMEN Y., KORKMAZ E., ZORA M.

SYNTHETIC COMMUNICATIONS, cilt.51, sa.4, ss.541-552, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 51 Sayı: 4
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1080/00397911.2020.1837171
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, EMBASE
  • Sayfa Sayıları: ss.541-552
  • Anahtar Kelimeler: 1, 4-oxazepines, N-propargylic &#946, -enaminones, sulfenylation, organosulfur compounds, alkynes, cyclization, ONE-POT SYNTHESIS, HIV-1 REVERSE-TRANSCRIPTASE, ELECTROPHILIC CYCLIZATION, PGE(2) ANTAGONIST, RECEPTOR-BINDING, INHIBITORS, DERIVATIVES, AMOXAPINE, ACIDS, DIACYLHYDRAZINE
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

A one-pot process for the synthesis of 6-[(4-nitrophenyl)thio]-substituted 2-methylene-2,3-dihydro-1,4-oxazepines is reported. When reacted with 4-nitrobenzenesulfenyl chloride, N-propargylic beta-enaminones afforded alpha-sulfenylated N-propargylic beta-enaminones, which, in the presence of zinc chloride, underwent electrophilic cyclization to yield 6-[(4-nitrophenyl)thio]-substituted 2-methylene-2,3-dihydro-1,4-oxazepines. Process was found to be general for various N-propargylic beta-enaminones along with large substrate scope and high functional group tolerance. This operationally easy method may provide quick access to a library of functionalized 1,4-oxazepines of pharmacological interest.