A convenient synthesis of 1,4-benzothiazepines from 1,3-benzothiazines via the ring transformation of -lactam-condensed 1,3-benzothiazine derivatives

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A convenient synthesis was devised for rare 2,3-disubstituted 4,5-dihydro-1,4-benzothiazepines from 2-aryl-4H-1,3-benzothiazines. The Staudinger reaction of 1,3-benzothiazines obtained with chloroacetyl chloride selectively furnished trans-monochloro β- lactam-condensed thiazines. The ring expansion of azeto[2,1-b][1,3]benzothiazin-1-one derivatives with sodium methoxide afforded 1,4-benzothiazepines as the sole product in good yields. The structures of the new molecules were proved by means NMR and IR spectroscopy.

Original languageEnglish
Article numberT07910SS
Pages (from-to)2943-2948
Number of pages6
JournalSynthesis
Issue number17
DOIs
Publication statusPublished - Sep 1 2010

    Fingerprint

Keywords

  • -lactams
  • 1,3-benzothiazine
  • 1,4-benzothiazepine
  • S,N-heterocycles
  • ring expansion

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this