Ultrasound-promoted synthesis of novel fused heterocycles by criss-cross cycloaddition

Abstract

This work reports a novel and highly efficient methodology for the synthesis of perhydrotriazolotriazoledithions from two successive 1,3-dipolar cycloaddition under ultrasound irradiation. Aromatic 2,3-diazabuta-1,3-diene ligands with thiocyanates in glacial AcOH produced the corresponding perhydro [1,2,4] triazolo [1,2-a] [1,2,4] triazole-1,5-dithiones via criss-cross cycloaddition reactions under ultrasound irradiation. Structures of all compounds were characterized by 1H and 13C NMR, UV, IR and elemental analysis spectral data. The major advantages of the reported method are its selectivity, operational simplicity, extremely mild reaction conditions, short reaction times, and excellent yields.

Keywords

• Cycloaddition
• Azine
• Heterocycle
• Ultrasound irradiation