Collect. Czech. Chem. Commun.
2002, 67, 1669-1680
https://doi.org/10.1135/cccc20021669
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
Abstract
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.
