Département de chimie moléculaire

An original route to 2-alkyamino-4-phenylquinazolines, e.g., I (X-rays crystal structure shown), in three steps from simple (hetero)arom. amines is reported here. The key step involves the intramol. cyclization of benzoyl arylguanidines (prepn. shown) performed in [OMIm]Cl ionic liq. The basic (hetero)arom. guanidines deprotonate the imidazolium-based ionic liq., thus triggering the cascade process ultimately leading to the intramol. 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. [on SciFinder(R)]