Preparation of Isoindolones by a Lithium-Iodide Exchange-Induced Intra­molecular Wurtz-Fittig Reaction of o-Iodobenzoyl Chloride/Imine Adducts

James B. Campbell*, Robert F. Dedinas, Sally Trumbower-Walsh

*Lead Generation Department, CNS Discovery, AstraZeneca Pharmaceuticals, Wilmington, DE 19850-5437, USA, Email: campbelljim.jbcgmail.com

J. B. Campbell, R. F. Dedinas, S. Trumbower-Walsh, Synlett, 2010, 3008-3010.

DOI: 10.1055/s-0030-1259061

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Abstract

Addition of o-iodobenzoyl chlorides to imines affords N-acyliminium ions as adducts. Subsequent reaction of these adducts with phenyllithium at -78˚C followed by warming to ambient temperature induces an intramolecular Wurtz-Fittig coupling to afford 2,3-dihydroisoindolones in excellent yields.

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Key Words

metal-halogen exchange, Wurtz-Fittig reaction, isoindolones, imines, acid chloride, isoindolinones

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ID: J60-Y2010-3410