Synthesis of 2-Azido-1,3-thiazoles as 1,2,3-Triazole Precursors

Abstract

By diazotization of 2-aminothiazoles and reaction with sodium azide, the derivatives of 2-azidothiazole were synthesized. Conditions of diazotization were selected according to the nature of a substituent in thiazoles. 2-Azidothiazole derivatives were studied in the base-catalysed condensation reactions with activated methylenic compounds to yield new 1-(1,3-thiazol-2-yl)-1H-1,2,3-triazole-4-carboxylic acids.

Keywords:

• Azides
• cyclocondensation
• thiazoles
• 1,2,3-triazoles

Notes

^a Isolated yields are based on single experiment and the yields were not optimized.

^b No reaction.

^c Mixture of H₃PO₄ (80%) and concentrated HNO₃ (2.2:1 by volume).

^a All melting points are given for crude products without purification and are uncorrected.

^b IR spectra were recorded in CCl₄ solution.