One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones: Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A

Org Lett. 2016 Jul 1;18(13):3070-3. doi: 10.1021/acs.orglett.6b01166. Epub 2016 Jun 10.

Abstract

An annulation of arylthioamides with 3-bromopyruvic acid chloride to 5-hydroxy-4H-1,3-thiazin-4-ones has been developed. The initial condensation affords two regioisomeric thiazolinone intermediates in a temperature-dependent manner. The synthesis of the 2-aminophenylthiazinone derivative led to the revision of the previously proposed structure of thiasporine A. Synthesis of the revised structure and NMR analysis revealed that thiasporine A had been isolated as a carboxylate.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Thiazines / chemical synthesis*
  • Thioamides / chemistry

Substances

  • Carboxylic Acids
  • Thiazines
  • Thioamides
  • thiasporine A