78695-87-1Relevant academic research and scientific papers
Antitumour Imidazotetrazines. Part 12. Reactions of Mitozolomide and its 3-Alkyl Congeners with Oxygen, Nitrogen, Halogen, and Carbon Nucleophiles
Baig, Ghouse Unissa,Stevens, Malcolm F. G.
, p. 665 - 670 (2007/10/02)
Mitozolomide (1) and its 3-alkyl congeners ring-open in aqueous sodium carbonate to form 5-(3-alkyltriazen-1-yl)imidazole-4-carboxamides.The 3-methyl and 3-ethyl analogues of mitozolomide decompose in alcohols to form 2-azahypoxanthine and 5-amino-1-alkoxycarbonylimidazole-4-carboxamides.In hydrazine hydrate mitozolomide yields, principally, 5-azidoimidazole-4-carboxamide, whereas the 3-alkyl-derivatives form 5-amino-4-carbamoylimidazole-1-carbohydrazide. 5-Diazoimidazole-4-carboxamide, generated by thermolysis of mitozolomide in acetic acid or pyridine, can be trapped by reactive methylenic ketones, nitriles or esters to afford imidazotriazines.
Triazines and Related Products, Part 22. Synthesis and Reactions of Imidazotriazines
Baig, Ghouse Unissa,Stevens, Malcolm F. G.
, p. 1424 - 1432 (2007/10/02)
5-Diazoimidazole-4-carboxamide couples with reactive methylenic substrates to afford a series of imidazolylhydrazones which cyclise in acid or alkali to imidazotriazines.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-carbamoylimidazotriazine-6-carboxylate hydrolyses in boiling 2N-hydrochloric acid, forms an N-acetyl derivative, and reacts with secondary heteroalicyclic amines to form amides.
