A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides

An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the prese...

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Bibliographic Details
Published in:Tetrahedron letters 2011-06, Vol.52 (26), p.3287-3290
Main Authors: Majce, Vita, Kočevar, Marijan, Polanc, Slovenko
Format: Article
Language:English
Subjects:
Acetonitrile
Aliphatic compounds
Amine catalysis
Chemistry
Exact sciences and technology
Fumaramides
Fumaric acid
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Isomerization
Kinetics and mechanisms
Microwave irradiation
Microwaves
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Reactors
Solvents
Synthesis (chemistry)
Tetrahedrons
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Description
Summary:An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the presence of a catalytic amount of piperidine, giving the corresponding fumaramides in high yields and purity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.04.066