Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones |
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Authors: | Cecilia Saiz Eduardo Manta S. Graciela Mahler |
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Affiliation: | a Laboratorio de Química Farmacéutica, DQO, Facultad de Química, Universidad de la República, Gral Flores 2124, CC 1157, Montevideo, Uruguay b Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA |
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Abstract: | A tandem method for the synthesis of 2-hydrazolyl-4-thiazolidinones (5) from commercially available materials in a 3-component reaction has been developed. The reaction connects aldehydes, thiosemicarbazides, and maleic anhydride, effectively assisted by microwave irradiation. The synthesis of a new type of compound, 2-hydrazolyl-5,5-diphenyl-4-thiazolidinone (7), obtained by treatment of thiosemicarbazone with benzil in basic media is also reported. HOMO/LUMO energies, orbital coefficients, and charge distribution were used to explain the proposed reaction mechanism. |
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Keywords: | 2-Hydrazolyl-4-thiazolidinones 2-Hydrazolyl-5,5-diphenyl-4-thiazolidinones Microwave Tandem reactions |
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