Ortho vinylation of anilines via cyclopalladation: a new route to nitrogen heterocycles

✍ Scribed by Hiroshi Horino; Naoto Inoue

• Book ID: 104237765
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 200 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86304-8

✦ Synopsis

Preparation and chemical behaviors of cyclopalladated complexes of acetanilides were studied. Coupling reactions of these complexes with olefins afforded a variety of Z-substituted acetanilides which were subjected to intramolecular cyclization to quinolines. Syntheses of heterocyclic compounds by utilization of transition metal complexes have been carried out by way of 2-halogeneted anilines. 1,2,3 Direct introduction of carbonyl group or vinylic moieties on the ortho position of anilines is also important to obtain the potential intermediates which can be converted into indoles, quinolines, and their related heterocyclic compounds. 4 Cyclopalladation of benzylidene aniline5 and benzylamine derivatives6 provided