An efficient synthesis of styryl 1,3,4-thiadiazoles using Lawesson’s reagent and Propylphosphonic anhydride-precursors for bis heterocycles

Abstract

The compounds styryl 1,3,4-thiadiazoles were prepared adopting one and two step methodologies to optimize the yield of the products. The two-step methodology via benzohydrazide followed by treatment with Lawesson’s reagent in the presence of Propylphosphonic anhydride and triethylamine produced styryl 1,3,4-thiadiazoles in excellent yields. The olefin moiety in these compounds is utilized to develop pyrazole and isoxazole rings by 1,3-dipolar cycloaddition methodology followed by oxidation.

Keywords

• Nitrile imine
• Nitrile oxide
• Manganese dioxide
• Pyrazolyl thiadiazole
• Isoxazolyl thiadiazole