Action of acrylonitrile on 4-cyano- and 4-carbethoxy pyridazin-3(2H)-ones and their 3-mercapto derivatives. A novel Synthesis of Pyrano and Thiinopyridazines

Reaction of acrylonitrile with 4-cyano-5,6-diphenyl pyridazin-3(2H)-one and 3(2H)-thione derivative ( 1a, b ) at elevated temperature gave 7H-5-amino-6-cyano-3,4-diphenylpyrano and thiino [2,3-c] pyridazines ( 2a, b ), respectively. However, the reaction of 4-carbethoxy pyridazine derivatives ( 1c, d ) with the same reagent, under the same conditions afforded 6H, 7H-6-cyano-3,4-diphenyl-5-oxopyrano ( 3a ) and thiino [2,3-c] pyridazine ( 3b ), respectively. In addition, treatment of ( 1a, c ) and ( 1b, d ) with acrylonitrile ar reflux in alkaline medium give the respective 3-(2′-cyanoethyloxo) ( 7a, c ) and 3-2′-cyanoethylthio ( 7b, d ) pyridazine derivatives. Prolonged alkaline hydrolysis of either ( 1a, c ) or ( 7a, c ) yielded the same product ( 8a ). Also hydrolysis of ( 1b, d ) and ( 7b, d ) afforded one and the same product ( 8b ). The structures of the products were assigned on the basis of satisfactory analytical and spectroscopic data.