Synthesis of pyrazolo [4,5]pyridazine and isoxazolo [3,4d]pyridazine derivatives

Arylhydrazones of diethylacetondicarboxylate3 was treated with formaldehyde to give 1-aryl-4,5,6-trihydropyridaine derivatives4a-f Cyclization of compound4a-f by hydroxylamine afforded [3,4d] 1,3,4,5-tetrahydropyridazine derivatives5a-f. Also cyclization of compound4c with semicarbazide gave 1-amidopyrazolo-5-one-1-aryl-3-carboxypyridazine6. On the other hand compound3 reacted with ethylorthoformate to give diethyl-1,4-dihydro-1-arylpyridazine-4-one-2,5 dicarboxylate7, which on treatment with hydrazine, semicarbazide and thiosemicarbazide gave pyridazine, amido and thioamido derivatives. The spectral and antimicrobial data of these compounds1–8 were studied.