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Synthesis 2015; 47(02): 193-198
DOI: 10.1055/s-0034-1379234
DOI: 10.1055/s-0034-1379234
paper
Convenient Synthesis of 2-[2-Aryl-2-oxo-1-(2-oxoindolin-3-ylidene)ethyl]fumarates via a One-Pot, Two-Step Reaction
Further Information
Publication History
Received: 10 July 2014
Accepted after revision: 12 September 2014
Publication Date:
29 October 2014 (online)
Abstract
The one-pot, two-step reactions of 4-picoline, a dialkyl acetylenedicarboxylate, and a 2-oxoindolin-3-ylidene derivative in 1,2-dimethoxyethane at elevated temperatures afford polyfunctionalized 2-[2-aryl-2-oxo-1-(2-oxoindolin-3-ylidene)ethyl]fumarates in moderate to good yields. The reaction mechanism involves the sequential formation of Huisgen’s 1,4-dipole, Michael addition, and loss of the pyridyl moiety.
Key words
multicomponent reaction - electron-deficient alkynes - isatin - fumarate - Huisgen’s 1,4-dipoleSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084. Included are 1H and 13C NMR spectra for all new compounds.
- Supporting Information
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