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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Authors: | Bolognese Adele Correale Gaetano Manfra Michele Lavecchia Antonio Novellino Ettore Barone Vincenzo |
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Institution: | Dipartimento di Chimica Organica e Biochimica, Universita di Napoli "Federico II", Napoli, Via Cynthia 6, Monte Sant'Angelo, I-80126, Napoli, Italy. bologne@unina.it |
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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. |
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