Journal of the Chemical Society. Perkin transactions I p. 1424 - 1432 (1981)
Update date:2022-08-04
Topics:
Baig, Ghouse Unissa
Stevens, Malcolm F. G.
5-Diazoimidazole-4-carboxamide couples with reactive methylenic substrates to afford a series of imidazolylhydrazones which cyclise in acid or alkali to imidazo<5,1-c><1,2,4>triazines.Hydrazones with cyano-substituents cyclise in acid to yield 7-aminoimidazotriazines whereas hydrazones with acetyl groups undergo acidic dehydration to form bicycles with a 7-methylene substituent.In basic conditions, hydrazones with a reactive ester group cyclise to imidazotriazin-7(4H)-ones with loss of an alcohol moiety.Ethyl 7-amino-3-carbamoylimidazo<5,1-c><1,2,4>triazine-6-carboxylate hydrolyses in boiling 2N-hydrochloric acid, forms an N-acetyl derivative, and reacts with secondary heteroalicyclic amines to form amides.
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