Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 6, Pages 2092-2095Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo902726k
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Funding
- Region Rhone-Alpes (cluster chimie)
- Departement de Chimie Moleculaire
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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.
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