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Communication | Special issue | Vol 74, No. 1, 2007, pp.145-148
Published online, 4th September, 2007
DOI: 10.3987/COM-07-S(W)19
Effective Synthetic Routes to 4H- and 10bH-Pyrido[2,1-a]isoindol-6-ones

Robert D. Dura, Isabelle Modolo, and Leo A. Paquette*

*Department of Chemistry, The Ohio State University, 100 West 18th Avenue Columbus, Ohio 43210, U.S.A.

Abstract

Two previously unknown pyridoisoindolones have been synthesized from N-allylphthalimide as the common precursor. The methodologies allowing these constructions include a novel twofold dehydrobromination involving an N-acyliminium ion that experiences regiocontrolled hydration. The synthetic routes are completed by indirect introduction of the diene unit.