ABSTRACT Several new 2‐(1,2,3‐triazol‐4‐yl)‐1,3,4‐oxadiazol‐2‐yl)thio)‐1‐arylethan‐1‐ones were synthesized in excellent yields using simple procedures. Reaction of 1‐(4‐fluorophenyl)‐5‐methyl‐1 H ‐1,2,3‐triazole‐4‐carbohydrazide ( 1 ) with carbon disulfide in ethanol and in the presence of potassium hydroxide at 0°C to room temperature for 6 h gave potassium 2‐(1‐(4‐fluorophenyl)‐5‐methyl‐1 H ‐1,2,3‐triazole‐4‐carbonyl)hydrazine‐1‐carbodithioate ( 2 ) as an intermediate. Subsequent in situ treatment of 2 with aqueous ethanol under reflux for 6 h, followed by neutralization with hydrochloric acid, gave 5‐(1‐(4‐fluorophenyl)‐5‐methyl‐1 H ‐1,2,3‐triazol‐4‐yl)‐1,3,4‐oxadiazole‐2‐thiol ( 3 ) in 70% yield. Reactions of thiol 3 with various phenacyl bromides 4 in ethanol in basic medium under reflux for 5 h gave the corresponding 2‐(1,2,3‐triazol‐4‐yl)‐1,3,4‐oxadiazol‐2‐yl)thio)‐1‐arylethan‐1‐ones 5a – f in 83%–88% yields. The structures of the newly synthesized heterocycles were elucidated using spectroscopic data and single‐crystal x‐ray structure determination. The intermolecular interactions in the crystal structures were explored.
Abdel‐Wahab et al. (Sun,) studied this question.