Convenient modification of the Leimgruber-Batcho indole synthesis: reduction of 2-nitro-β-pyrrolidinostyrenes by the FeCl3–activated carbon–N2H4∙H2O system

A new catalytic system containing ferric chloride, activated carbon, and hydrazine has been proposed for the reductive cyclization of β-dialkylamino-2-nitrostyrenes to give the corresponding indoles (Leimgruber-Batcho synthesis). Various substituted indoles may be obtained in high yield under these...

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Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 47; no. 4; pp. 425 - 434
Main Authors Taydakov, I. V., Dutova, T. Ya, Sidorenko, E. N., Krasnoselsky, S. S.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.07.2011
Subjects
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
indoles
reductive cyclization
enamines
β-dialkylamino-2-nitrostyrenes
Leimgruber-Batcho synthesis
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Summary:A new catalytic system containing ferric chloride, activated carbon, and hydrazine has been proposed for the reductive cyclization of β-dialkylamino-2-nitrostyrenes to give the corresponding indoles (Leimgruber-Batcho synthesis). Various substituted indoles may be obtained in high yield under these conditions.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-011-0776-2