Microwave assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones.
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.
Saiz
Cecilia
C
Laboratorio de Química Farmacéutica, DQO, Facultad de Química, Universidad de la República, Gral Flores 2124, CC 1157, Montevideo Uruguay.
Pizzo
Chiara
C
Manta
Eduardo
E
Wipf
Peter
P
Mahler
S Graciela
SG