N-Capping of Primary Amines with 2-Acyl-benzaldehydes to give Isoindolinones

DANIEL AUGNER; DARÍO C. GERBINO; NIKOLAY SLAVOV; JÖRG M. NEUDÖRFL; HANS G. SCHMALZ

ORGANIC LETTERS

AMER CHEMICAL SOC

Año: 2011 vol. 13 p. 5374 - 5377

1523-7060

A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. Itwas shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As thesubstrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.