Staudinger and retro-Staudinger reactions. The dichloro-β-lactam moiety as a useful handle for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The dichloro-β-lactam ring, obtained via Staudinger reaction of 4-aryl-2H-1,3-benzothiazines, proved to be a useful protecting strategy for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides. After oxidation of the 1,1-dichloroazeto[2,1-c][1,3]-benzothiazin-2-ones, the thiazine ring could be recovered selectively and in good yield by treatment with base. Thus, novel 4-aryl-2H-1,3-benzothiazine 1,1-dioxides were obtained efficiently.

Original languageEnglish
Pages (from-to)3205-3207
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number24
DOIs
Publication statusPublished - Jun 16 2010

    Fingerprint

Keywords

  • 1,3-Benzothiazine
  • Dichloro-β-lactam
  • Oxidation
  • Staudinger reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this