Microwave-Promoted Syntheses of Quinazolines and Dihydroquinazolines from 2-Aminoarylalkanone O-Phenyl Oximes

Fernando Portela-Cubillo, Jackie S. Scott and John C. Walton*

*School of Chemistry, University of St. Andrews, EaStChem, St. Andrews, Fife KY16 9ST, U.K., Email: jcwst-and.ac.uk

F. Portela-Cubillo, J. S. Scott, J. C. Walton, J. Org. Chem., 2009, 74, 4934-4942.

DOI: 10.1021/jo900629g

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Abstract

A rapid and convenient free-radical-based synthesis of functionalized quinazolines relies on microwave-promoted reactions of O-phenyl oximes with aldehydes in the presence of ZnCl₂. The method worked well with alkyl, aryl, and heterocyclic aldehydes and for a variety of substituents in the benzenic part of the molecule.

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Key Words

quinazolines, microwave synthesis, ionic liquids

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ID: J42-Y2009-2080