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Paper | Regular issue | Vol 83, No. 5, 2011, pp.1029-1040
Published online, 25th March, 2011
DOI: 10.3987/COM-11-12141
Synthesis, Theoretical Study, and Antimicrobial Activity of Novel Polysubstituted Thiazoles

Nadia Hanafy Metwally* and Sabry El-Taher

*Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Abstract

New 5-(9H-Fluoren-9-ylidene)- and 5-(1H-indan-1-ylidene)-2-thioxo-4-thiazolidinones 3a,b were synthesized Eco-friendly under microwave irradiation (MWI). These compounds undergo alkaline hydrolysis to afford the corresponding thiol derivatives 4a,b, which cyclized into polysubstituted thiazoles 6a-h using arylazomalononitriles 5a-d as nucleophilic agents. Some selected products were tested for their antimicrobial activities. The equilibrium geometries of the studied compounds were calculated at the B3LYP/6-31G(d) level of the density functional theory (DFT). Conformational analysis has been carried out to determine the most stable conformers. The relative stability of the azo and hydrazo tautomers has been investigated. The HOMO-LUMO energy gap is used in rationalizing the reactivity of the studied compounds.