%0 Journal Article
%@ 0040-4039
%A Saiz, C
%A Pizzo, C
%A Manta, E
%A Wipf, P
%A Mahler, SG
%D 2009
%F pittir:19215
%J Tetrahedron Letters
%N 8
%P 901 - 904
%T Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones
%U http://d-scholarship-dev.library.pitt.edu/19215/
%V 50
%X 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.