Copper-catalyzed tandem reaction between imines and alcohols leading to indoles

Graphic A copper-catalyzed tandem reaction between 2-alkynyl- N-arylideneanilines and alcohols is found to produce N-(alkoxybenzyl)indoles in good to high yields. A wide variety of substituted N-(alkoxybenzyl)indole derivatives can be synthesized by utilizing this protocol, since the derived indoles...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 1; pp. 35 - 38
Main Authors Kamijo, Shin, Sasaki, Yuya, Yamamoto, Yoshinori
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 2004
Elsevier
Subjects
alcohol
alkyne
Chemistry
Chemistry, Organic
copper catalyst
imine
indole
Physical Sciences
Science & Technology
alcohol
copper catalyst
alkyne
indole
imine
PALLADIUM
2-SUBSTITUTED INDOLES
BIMETALLIC CATALYST
O-ALKYNYL(OXO)BENZENES
LEWIS-ACID
ALKYNES
2-ALKYNYLANILINES
4+2 CYCLOADDITION
HETEROAROMATIC RING-SYSTEMS
CYCLIZATION
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Summary:Graphic A copper-catalyzed tandem reaction between 2-alkynyl- N-arylideneanilines and alcohols is found to produce N-(alkoxybenzyl)indoles in good to high yields. A wide variety of substituted N-(alkoxybenzyl)indole derivatives can be synthesized by utilizing this protocol, since the derived indoles are essentially formed by the four-component assemblies of aldehydes, 2-iodoanilines, terminal alkynes, and alcohols.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.10.141