Pyridazine derivatives and related compounds, part 9. tetrazolo[1,5-b]pyridazine-8-carbohydrazide: synthesis and some reactions.
The reaction of the hydrazide of 6,7-diphenyltetrazolo[1,5-b]pyridazine-8-carboxylic acid 3 with aromatic aldehydes gave 8-arylidenecarbohydrazide derivatives. The reaction of 3 with methanesulfonyl chloride, benzenesulfonyl chloride, phenyl and benzylisothiocyanate afforded the corresponding N-substitute derivatives. The reaction of 3 with potassium ethylxanthate gave 5-(6,7-diphenyltetrazolo[1,5-b]pyridazin4-yl)-1,3,4-oxadiazole-2-thione 7. The alkylation of this product in an alkaline medium proceeds at the sulfur atom, while the aminomethylation and acylation proceed at the nitrogen atom. Compound 3 was also reacted with N-aminothiosemicarbazide to give 5-(6,7-diphenyltetrazolo[1,5-b]pyridazin-8 yl)4-amino-1,2,4-triazole-3-thione 11.
Department of Chemistry, Faculty of Science, Zagazig University, Egypt.
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D000478:Alkylation; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011724:Pyridazines / Q000138:chemical synthesis* / Q000737:chemistry
D006834:Hydrazines; D007202:Indicators and Reagents; D011724:Pyridazines; C464592:trazolo(1,5-b)pyridazine-8-carbohydrazide