Syntheses of 4-(3-Cyano-1-triazeno) pyridazine 1-Oxides Related Compounds

Abstract

4-(3-Cyano-1-triazeno) pyridazine 1-oxides (IIIa-d), 3, 6-dimethyl-4-(3-cyano-1-triazeno) pyridazine 2-oxide and 6-(3-cyano-1-triazeno) tetrazolo [1, 5-b] pyridazine were synthesized by treating the corresponding azides with potassium cyanide, followed by acidification with hydrochloric acid. 4-(3-Cyano-1-triazeno) pyridazine 1-oxide potassium salts (IIa, IIb) gave pyridazine 1-oxides (Va, Vb) on treatment with a mixture of hydrochloric acid and ethanol, and on treatment with hydrochloric acid alone, they gave a mixture of 4-chloropyridazine 1-oxides (VIa, VIb) and 4-aminopyridazine 1-oxides (VIIa, VIIb). The reaction of the cyanotriazene potassium salt (IIa) and hydroxylamine hydrochloride gave 4-[3-(N²-hydroxyamidino)-1-triazeno] pyridazine 1-oxide (X), and a similar compound (XIIa) was also prepared. An azourethan, 3, 6-dimethyl-4-[3-(ethoxycarbonyl)-1-triazeno] pyridazine 2-oxide (XIIb) and an azourea, 6-(3-carbamoyl-1-triazeno) tetrazolo [1, 5-b] pyridazine (XV) were synthesized from the corresponding cyanotriazene potassium salts. Arylazopyridazine 1-oxides (VIIIa-g) and 2-oxides (IXa, b) were synthesized by treating the cyanotriazene potassium salts (IIa-d, XI) with a mixture of 2-naphthol or diphenylamine and ethanol containing hydrochloric acid.