1,3-Dipolar cycloadditions of 1-(N-arylidene)amino-1, 2,3-triazoles with diphenylnitrilimine

Abstract

1-(N-Arylidene)amino-1,2,3-triazoles (1) and (9) react with diphenylnitrilimine (2) to give the corresponding 1,2,3- and 1,2,4-triazoles (3) and (4) as well as 1- and 2-benzohydrazonoyl-1,2,3-triazoles (5), (10) and (6) and (11) respectively. These products are formed assuming an initial cycloadduct, (7), which upon elimination of the triazole ring gives compounds (3) and (4). Further reaction of the triazole system with (2) gives the hydrazone derivatives (5), (6), (10), and (11). The reaction is also studied on the basis of frontier molecular orbitals (FMO) of the reacting species.