Aryliodoazide Synthons: A Different Approach for Diversified Synthesis of 2-Aminothiazole, 1,3-Thiazole, and 1,3-Selenazole Scaffolds

ACS Comb Sci. 2019 Jul 8;21(7):516-521. doi: 10.1021/acscombsci.9b00045. Epub 2019 Jun 18.

Abstract

Several straightforward and practical processes have been established for the construction of 2-aminothiazoles, 1,3-thiazoles and 1,3-selenazoles from aryliodoazides. These strategies successfully proceed with a wide spectrum of substituted thioamides and its derivatives producing the resulting five-membered heterocycles obtained in satisfactory yields. The unique features of these protocols are operational simplicity and highly functional group tolerance, which make them convenient and practical routes for the preparation of various libraries of 2-aminothiazoles, 1,3-thiazoles, and 1,3-selenazoles.

Keywords: 1,3-selenazole; 1,3-thiazole; 2-aminothiazole; iodoazide; isothiocyanate; selenoamide; thioamide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Azoles / chemical synthesis*
  • Azoles / chemistry
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Iodinated / chemistry*
  • Molecular Structure
  • Organoselenium Compounds
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • 1,3-selenazole
  • Azides
  • Azoles
  • Hydrocarbons, Iodinated
  • Organoselenium Compounds
  • Thiazoles