Saiz, C and Pizzo, C and Manta, E and Wipf, P and Mahler, SG
(2009)
Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones.
Tetrahedron Letters, 50 (8).
901 - 904.
ISSN 0040-4039
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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. © 2008 Elsevier Ltd.
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