87864-82-2Relevant academic research and scientific papers
Reactions of 4-Cyano- and 4-Methylimidazoles with Isocyanates
Mitsuhashi, Keiryo,Itho, Ei-ichi,Kawahara, Takeo,Tanaka, Kiyoshi
, p. 1103 - 1106 (2007/10/02)
4-Cyano- and 4-methylimidazoles reacted with methyl and aryl isocyanates to give exclusively 1-(substituted carbamoyl)-4-cyano- and 4-methylimidazoles, respectively.Refluxing of 1-carbamoyl-4-methylimidazoles in nitrobenzene yielded 2-carbamoyl-4-methylimidazoles through a known migration, whereas the 4-cyano analogues could not be caused to migrate.On the other hand, the treatment of 4-cyano-1-(methylcarbamoyl)imidazole with methyl isocyanate under the basic conditions resulted in the formation of 2-methyl-1-(methylcarbamoylimino)-2,3-dihydro-1H-imidazoimidazol-3-one which must be formed via the migration of the carbamoyl group to another nitrogen followed by the intramolecular cyclization of the newly introduced carbamoyl group with its vic cyano group.
