Synthesis of Two Isomeric Thiadiazine and Thiazole Derivatives from a Hydrazonoyl Halide

Abstract

Thiadiazine and thiazoles have attracted importance due to their broad applicability as biologically active compounds. New thiadiazines and thiazoles are prepared via the simple reaction of an α-haloketohydrazonoyl with thiocarbohydrazone derivatives in a basic medium under reflux. A S-alkylated intermediate forms through nucleophile substitution involving the hydrazonoyl halogen and thiocarbohydrazone thiol. In situ cyclization via the condensation between the carbonyl and NH₂ or NH moieties of the intermediate forms 1,3,4-thiadiazine and thiazole derivatives, respectively. This method employs inexpensive, commercially available reagents and facile reaction conditions to afford novel thiadiazine/thiazole derivatives in good yields.

Keywords:

• Hydrazonoyl
• thiocarbohydrazone
• thiadiazine
• thiazole

Additional information

Funding

The authors are grateful to the Department of Chemistry, King Faisal University, for their help and support for this study.