Novel Thiazolactone Derivatives: Synthesis and Quantum Chemical Study

Abstract

In this research, 15 novel derivatives of the thiazolactone skeleton were synthesized using the Erlenmeyer–Plöchl reaction procedure. Glycine, alanine and leucine amino acids were used to make dithiocarbamate precursor by reacting amino acids with carbon disulfide and benzyl chloride. Obtained benzyl dithiocarbamate underwent thiazolactone formation in the presence of acetic anhydride and then condensed with arylglyoxals as condensing carbonyl group source. Products were characterized using their spectroscopic IR, 1H NMR, and 13C NMR data. In continuation, computational chemistry methods were used to get some information about the products such as structural characteristics, charge distribution, 1H NMR and UV-visible spectra. Results showed that the calculated chemical shifts are in good agreement with experimentally recorded ones. The B3LYP density functional method in conjunction with the 6-311++G(d,p) basis set was used for all calculations.