Collect. Czech. Chem. Commun. 1999, 64, 408-416

Intramolecular Mannich Reaction of 2-Oxotryptamines with Acetone Yielding Spiro[indole-3,3'-pyrrolidin]-2-ones

Mária Incze, Gábor Dörnyei, Mária Kajtár-Peredy and Csaba Szántay*

Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1025 Budapest II., Pusztaszeri út 59-67 H-1525 Budapest, P.O. Box 17, Hungary


2-Oxotryptamines undergo intramolecular Mannich-type cyclization with acetone to give 2',2'-dimethylspiro[indole-3,3'-pyrrolidin]-2-ones. In presence of an alkylating reagent, this reaction gives the corresponding 1'-substituted products.

Keywords: Intramolecular Mannich reaction; Spirocyclic compounds; Indoles; Pyrrolidines; Cyclizations; Alkaloids.