Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction
2013
Abstract
Treatment of 3-hydroxyoxindoles with trichloroacetonitrile (1.3 equiv.) and a catalytic amount of DBU (0.1 equiv.) followed by addition of nucleophiles (1.5 equiv.) and diphenylphosphoric acid (0.2 equiv.) afforded the 3,3-disubstituted oxindoles in good to excellent yields. DFT computations supported the notion that the reaction went through the 1-alkyl-2-oxo-2H-indol-1-ium intermediate.
Details
Title
Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction
Author(s)
Piemontesi, Cyril ; Wang, Qian ; Zhu, Jieping
Published in
Organic & Biomolecular Chemistry
Pagination
4
Volume
11
Issue
9
Pages
1533
Date
2013
Publisher
Cambridge, Royal Soc Chemistry
ISSN
1477-0539
Other identifier(s)
View record in Web of Science
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Work produced at EPFL
Journal Articles
Published
Work produced at EPFL
Journal Articles
Published
Record creation date
2013-02-08