American Chemical Society
ol202271k_si_001.pdf (15.51 MB)

N-Capping of Primary Amines with 2-Acyl-benzaldehydes To Give Isoindolinones

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journal contribution
posted on 2011-10-07, 00:00 authored by Daniel Augner, Dario C. Gerbino, Nikolay Slavov, Jörg-Martin Neudörfl, Hans-Günther Schmalz
A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford 3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As the substrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.