title: N-Capping of primary amines with 2-acyl-benzaldehydes to give isoindolinones.
abstract: 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.
authors: Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany.
authors: Daniel
authors: D
authors: Augner
authors: Dario C
authors: DC
authors: Gerbino
authors: Nikolay
authors: N
authors: Slavov
authors: Jörg-Martin
authors: JM
authors: Neudörfl
authors: Hans-Günther
authors: HG
authors: Schmalz
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D054833:Isoindoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D054833:Isoindoles; D001554:Benzene