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Issue 19, 2004
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Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating

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Abstract

Microwave irradiation of a mixture of benzylidene-anilines and mercaptoacetic acid in benzene gives 1,3-thiazolidin-4-ones in very high yield (65–90%), whereas the same reaction performed through using the conventional method, at reflux temperature, requires a much longer time and gives a much lower yield (25–69%). This difference seems to be due to some intermediates and by-products formed during the conventional reaction. On the basis of 1H NMR studies, two different mechanisms, acting in benzene and in DMF, respectively, have been hypothesized for the thiazolidin-4-one system formation.

Graphical abstract: Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating

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Article information


Submitted
13 Apr 2004
Accepted
14 Jul 2004
First published
03 Sep 2004

Org. Biomol. Chem., 2004,2, 2809-2813
Article type
Paper

Thiazolidin-4-one formation. Mechanistic and synthetic aspects of the reaction of imines and mercaptoacetic acid under microwave and conventional heating

A. Bolognese, G. Correale, M. Manfra, A. Lavecchia, E. Novellino and V. Barone, Org. Biomol. Chem., 2004, 2, 2809
DOI: 10.1039/B405400H

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