Reactions of 4‐cyano‐ and 4‐methylimidazoles with isocyanates

Keiryo Mitsuhashi, Ei‐Ichi Itho, Takeo Kawahara, Kiyoshi Tanaka

doi:10.1002/jhet.5570200452

Reactions of 4‐cyano‐ and 4‐methylimidazoles with isocyanates

DOI Web Site Web Site 被引用文献1件

書誌事項

公開日: 1983-07

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/jhet.5570200452

公開者: Wiley

この論文をさがす

CiNii Books

説明

<jats:title>Abstract</jats:title><jats:p>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‐1<jats:italic>H</jats:italic>‐imidazo[1, 5‐<jats:italic>c</jats:italic>]imidazol‐3‐one which must be formed <jats:italic>via</jats:italic> the migration of the carbamoyl group to another nitrogen followed by the intramolecular cyclization of the newly introduced carbamoyl group with its <jats:italic>vic</jats:italic>cyano group.</jats:p>