2-Arylhydrazononitriles as building blocks in heterocyclic synthesis: A novel route to 2-substituted-1,2,3-triazoles and 1,2,3-triazolo[4,5-b]pyridines

Abstract

2-Arylhydrazono-3-oxobutanenitriles 2 was reacted with hydroxylamine hydrochloride to yield amidooxime 3. This was cyclized into the corresponding oxadiazole 4 on refluxing in acetic anhydride. When refluxed in DMF in presence of piperidine, the corresponding 1,2,3-triazoleamine 5 was formed. The latter was acylated to 6 by addition of acetic anhydride while treatment of 5 with malononitrile gave the 1,2,3-triazolo [4,5-b]pyridine 8. Treatment of acetyl derivative 6 with DMFDMA gave enaminone 9. The enaminone 9 was coupled with benzenediazonium chloride to yield phenylazo-1,2,3-triazolo [4,5-b]pyridine 10. Trials to convert compound 14 into 1,2,3-triazolo [4,5-d]pyrimidine 15 via refluxing in AcOH/NH4OAc failed. Instead the hydrolyzed product 5 was formed.