THE REACTIONS OF 3-DIAZOPYRAZOLO{[}3,4-B]PYRIDINE DERIVATIVES WITH REACTIVE METHYLENE-COMPOUNDS

Diazotised 3,6-diamino-4-phenylpyrazolo{[}3,4-b]pyridine-5-carbonitrile, 2, reacted with active methylene reagents and with beta-naphthol to yield pyrido{[}3',2':4,5]pyrazolo{[}3,2-c]-1,2,4-triazine derivatives (4a-d) and a pyrido{[}3',2':4,5]pyrazolo{[}3,2-c]naphtho{[}2,1-e]-1,2,4-triazine derivative, 6, respectively. Compound 2 coupled with 3-methyl-5-pyrazolone and 1-phenyl-3-methyl-5-pyrazolone to yield the corresponding azo compounds (7a,b). Cyclisation of compound 7b yielded 8-chloro-3-methyl-1,6diphenylpyrido{[}3',2':4,5]dipyrazolo{[}3,2-c:3',4' -c]-1,2,4-triazine-7-carbonitrile, 9. Reaction of 2 with dimethyl acetylenedicarboxylate is also described.