Intramolecular Mannich reaction of 2-oxotryptamine and homologues with oxo reagents yielding spiro compounds. Part II

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-...

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Bibliographic Details
Published inCollection of Czechoslovak chemical communications Vol. 67; no. 11; pp. 1669 - 1680
Main Authors Dornyei, G, Incze, M, Kajtar-Peredy, M, Szantay, C
Format Journal Article
LanguageEnglish
Published PRAGUE 6 Inst Organic Chem And Biochem 01.01.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
oxindoles
cyclizations
intramolecular Mannich reaction
indoles
pyrrolidines
spirocyclic compounds
alkaloids
piperidines
ketones
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Summary: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.
ISSN:0010-0765
1212-6950
DOI:10.1135/cccc20021669