Copper-catalyzed ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids to 1,4-benzothiazines

Org Biomol Chem. 2015 Mar 14;13(10):3122-7. doi: 10.1039/c4ob02467b.

Abstract

A new ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids was developed, which allows for one-pot synthesis of 1,4-benzothiazines in moderate to excellent yields. The cascade reaction was achieved through decarboxylative coupling, nucleophilic ring-opening reaction and intramolecular hydroamination process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Solvents / chemistry
  • Temperature
  • Thiazines / chemical synthesis*
  • Thiazoles / chemistry*

Substances

  • 1,4-benzothiazine
  • Carboxylic Acids
  • Solvents
  • Thiazines
  • Thiazoles
  • Copper