Antitumour imidazotetrazines. Part 12. Reactions of mitozolomide and its 3-alkyl congeners with oxygen, nitrogen, halogen, and carbon nucleophiles
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 665-670
- https://doi.org/10.1039/p19870000665
Abstract
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 imidazo[1,2,4]triazines.This publication has 1 reference indexed in Scilit:
- Imidazoles. II. 5(or 4)-(Monosubstituted Triazeno)imidazole-4(or 5)-carboxamides1Journal of Medicinal Chemistry, 1966