Gold-Catalyzed Reactions of 2-Alkynyl-phenylamines with α,β-Enones

The gold-catalyzed reaction of 2-alkynyl-phenylamines with α,β-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to differe...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-03, Vol.70 (6), p.2265-2273
Main Authors: Alfonsi, Maria, Arcadi, Antonio, Aschi, Massimiliano, Bianchi, Gabriele, Marinelli, Fabio
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Catalysis
Chemistry
Exact sciences and technology
Gold - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Ketones - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
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Summary:The gold-catalyzed reaction of 2-alkynyl-phenylamines with α,β-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/α,β-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140 °C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo047793i