Condensed Pyridazines. VI. Reaction of 7- (Methylsulfonyl) 1-phenyl-1H-1, 2, 3-triazolo [4, 5-d] pyridazine with Carbanions and Enamines

The reaction of 7- (methylsulfonyl) -1-phenyl-1H-1, 2, 3-triazolo [4, 5-d] pyridazine (1) with active methylene compounds or ketones (3a-g) in the presence of sodium hydride gave the corresponding 7-substituted 1-phenyl-1H-1, 2, 3-triazolo [4, 5-d] pyridazines (4a-g). A [4 + 2] cycloaddition occurred in the reaction with enamines or ynamines (9a-d) to give the corresponding arenotriazoles (10a-d). Similarly, the reaction of 7-chloro-1-phenyl-1H-1, 2, 3-triazolo [4, 5-d] pyridazine (2) with 3 and 9 resulted in the formation of 4 and arenotriazoles (12), respectively.