50530-35-3Relevant academic research and scientific papers
1,3-Anionic Cycloadditions, XVII. Synthesis of Imidazolines and Imidazoles by Cycloaddition of 2-Azaallyllithium Compounds to Aromatic Nitriles
Kauffmann, Thomas,Busch, Alfred,Habersaat, Kai,Koeppelmann, Edgar
, p. 492 - 499 (2007/10/02)
1,3-Diphenyl-2-azaallyllithium (1c) reacts with aromatic nitriles by cycloaddition and subsequent dehydration to give lithiated imidazoles (3b). 1,1-Diphenyl-2-azaallyllithium (1a) under corresponding conditions gives either by cycloaddition lithiated imidazolines (2) or by normal addition lithiated open-chain enamines (5a, b).The enamines formed (4-amino-2-azabutadienes) are isolable in spite of their primary amino group. - Cycloaddition in preparatively useful yield was not possible with aliphatic nitriles.
