Département Chimie Moléculaire, UMR 5250 & FR 2607, CNRS/Université de Grenoble, BP 53, 38041 Grenoble Cedex 9, France.
J Org Chem. 2010 Mar 19;75(6):2092-5. doi: 10.1021/jo902726k.
An original route to 2-alkyamino-4-phenylquinazolines in three steps from simple (hetero)aromatic amines is reported here. The key step involves the intramolecular cyclization of benzoyl arylguanidines performed in [OMIm]Cl ionic liquid. The basic (hetero)aromatic guanidines deprotonate the imidazolium-based ionic liquid, thus triggering the cascade process ultimately leading to the intramolecular cyclization. This reaction is the first example of a Friedel-Crafts-type reaction in which an N-heterocyclic carbene is involved in the formation of the electrophilic intermediate.
本文报道了一种从简单（杂）芳基胺三步合成 2-烷氨基-4-苯基喹唑啉的新方法。关键步骤是在[OMIm]Cl 离子液体中环化苯甲酰芳基胍。碱性（杂）芳基胍使基于咪唑的离子液体去质子化，从而引发级联反应，最终导致分子内环化。该反应是首例涉及 N-杂环卡宾形成亲电中间体的傅-克型反应。
