866049-10-7Relevant academic research and scientific papers
Swift and efficient synthesis of 4-phenylquinazolines: Involvement of N-heterocyclic carbene in the key cyclization step
Debray, Julien,Leveque, Jean-Marc,Philouze, Christian,Draye, Micheline,Demeunynck, Martine
supporting information; experimental part, p. 2092 - 2095 (2010/06/16)
"Chemical Equation Presented" 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.
