Synthesis 2008(20): 3261-3266  
DOI: 10.1055/s-0028-1083141
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Simple Synthesis of New 2-Thioxoimidazolidine-4,5-dicarboxylates from Vicinal Diisothiocyanatocarboxylates

Dariusz Cież*a, Justyna Kalinowska-Tłuścika, Sandrine Peyratb, Elodie Pougoue Toukob, Bartosz Trzewika, Krzysztof Zwolińskia
a Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Kraków, Poland
Fax: +48(12)6340515; e-Mail: ciez@chemia.uj.edu.pl;
b Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans cedex 2, France
Further Information

Publication History

Received 3 June 2008
Publication Date:
25 September 2008 (online)

Abstract

A simple synthesis of novel symmetrical and unsymmetrical 2-thioxoimidazolidine-4,5-dicarboxylates is described. The symmetrical 2-thioxoimidazolidine-4,5-dicarboxylates were obtained through partial hydrolysis of vicinal 2,3-diisothiocyanato­carboxylates. The unsymmetrical 2-thioxoimidazolidine-4,5-dicarboxylates were prepared by addition of a stoichiometric amount of primary and secondary amines to vicinal 2,3-diisothiocyanatocarboxylates. The resulting imidazolidine derivatives were found to be convenient reactants for the construction of a new bicyclic imidazo[2,1-b]thiazole system. The addition of a twofold excess of amine to vicinal 2,3-diisothiocyanatocarboxylates gave rise to competitive condensations yielding bi-imidazolidine and bi-1,2,4-triazine derivatives.

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