Collect. Czech. Chem. Commun. 2007, 72, 1435-1445

Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives

Ladislav Janoveca, Stanislav Böhmb, Ivan Danihela, Ján Imricha,*, Pavol Kristiana and Karel D. Klikac

a Institute of Chemistry, Faculty of Science, P. J. Šafárik University, SK-04167 Košice, Slovak Republic
b Department of Organic Chemistry, Institute of Chemical Technology, Prague, CZ-16628 Prague 6, Czech Republic
c Department of Chemistry, University of Turku, FIN-20014 Turku, Finland


A regioselective synthesis of 3-alkyl-2-[(anthracen-9-yl)imino]thiazolidin-4-ones 2a-2e and 2-(alkylimino)-3-(anthracen-9-yl)thiazolidin-4-ones 3a-3e from appropriate thioureas using methyl bromoacetate or bromoacetyl bromide, respectively, has been rationalized by DFT calculations of model thiourea and its phenyl derivative. The proposed mechanism indicates that the regioselective formation of the target thiazolidinones is a consequence of a different reactivity of the reagents and a varying stability of the intermediates, 1-alkyl-3-(anthracen-9-yl)-2-[(methoxycarbonyl)methyl]isothioureas 4a-4e and 1-alkyl-3-(anthracen-9-yl)-2-(bromoacetyl)isothioureas 6a-6e.

Keywords: B3LYP functional; Bromoacetic acid; DFT calculations; Reaction mechanisms; Regioselectivity; Thiourea; Thiazolidinone.

References: 9 live references.