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Communication | Regular issue | Vol 78, No. 5, 2009, pp.1177-1181
Published online, 27th January, 2009
DOI: 10.3987/COM-08-11621
Facile Synthesis of 1-Aryl-2,3-dihydro-1H-isoindoles by Cyclization of N-Formyliminium Ion via Geometrically Disfavored 5-Endo-trig Process

Michikazu Kitabatake, Toshiaki Saitoh, Takehiro Sano, and Yoshie Horiguchi*

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


Synthesis of 1-aryl-2,3-dihydro-1H-isoindoles (isoindolines) (10) was achieved in a highly effective manner via acid catalyzed cyclization of N-formyliminium ion (8) obtained from 2,3-dimethoxybenzylamine and carbonyl compounds with acetic-formic anhydride under a one pot procedure. This Pictet-Spengler type reaction provides a convenient method for preparing 1-arylisoindolines.