Collect. Czech. Chem. Commun. 2002, 67, 1669-1680

Intramolecular Mannich Reaction of 2-Oxotryptamine and Homologues with Oxo Reagents Yielding Spiro Compounds. Part II

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

Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1025 Budapest II, Pusztaszeri út 59-67, Hungary


2-Oxotryptamine and its homo derivative undergo intramolecular Mannich-type cyclization with acetone and other ketones to give spiro[indole-3,3'-pyrrolidin]-2-ones and spiro[indole-3,3'-piperidin]-2-ones. A similar reaction with the bis-homologue of 2-oxotryptamine to yield spiro[azepane-3,3'-indol]-2'-ones was unsuccessful.

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

References: 18 live references.