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

Dariusz Cież; Justyna Kalinowska-Tłuścik; Sandrine Peyrat; Elodie Pougoue Touko; Bartosz Trzewik; Krzysztof Zwoliński

doi:10.1055/s-0028-1083141

PAPER

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

Dariusz Cież*^a, Justyna Kalinowska-Tłuścik^a, Sandrine Peyrat^b, Elodie Pougoue Touko^b, Bartosz Trzewik^a, Krzysztof Zwoliński^a
^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

Abstract

All articles of this category

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.

Key words

addition reaction - cyclisation - heterocycles - imidazolidines - vicinal diisothiocyanatocarboxylates

Full Text

References

1a Hirashima A. Shinkai K. Kuwano E. Taniguchi E. Eto M. Biosci., Biotechnol., Biochem. 1998, 62: 1179

1b Hirashima A. Pan C. Shinkai K. Tomita J. Kuwano E. Taniguchi E. Eto M. Bioorg. Med. Chem. 1998, 6: 903

1c Cetinkaya B. Cetinkaya E. Kuecuekbay H. Durmaz R. Arzneim.-Forsch. 1996, 46: 1154

1d Babayan VG. J. Appl. Chem. USSR (Engl. Transl.) 1985, 58: 1100

2 Knudsen KR. Risgaard T. Nishiwaki N. Gothelf KV. Jørgensen KA. J. Am. Chem. Soc. 2001, 123: 5843

3 Baumgartner H. O’Sullivan AC. Tetrahedron 1997, 53: 2775

4 Goubet F. Teutsch G. Tetrahedron 1996, 37: 7727

5a Lavielle S. Bory S. Moreau B. Luche MJ. Marquet A. J. Am. Chem. Soc. 1978, 100: 1558

5b Chen F.-E. Dai H.-F. Kuang Y.-Y. Jia H.-Q. Tetrahedron: Asymmetry 2003, 14: 3667

6 Megia EF. Sardina FJ. Tetrahedron Lett. 1997, 38: 673

7a Megia EF. Paz MM. Sardina FJ. J. Org. Chem. 1994, 59: 7643

7b Megia EF. Iglesias-Pintos JM. Sardina FJ. J. Org. Chem. 1997, 62: 4770

8 Ooi T. Kameda M. Fujji J. Maruoka K. Org. Lett. 2004, 6: 2397

9 Cież D. Tetrahedron 2007, 63: 4510

10 Joseph VB. Satchell DPN. Satchell RS. Wassef WN. J. Chem. Soc., Perkin Trans. 2 1992, 339

11 Altomare A. Cascarano G. Giacovazzo C. Guagliarch A. J. Appl. Crystallogr. 1993, 26: 343

12 Sheldrick GM. SHELX97. Programs for Crystal Structure Analysis University of Göttingen; Germany: 1997.

13 Farrugia LJ. J. Appl. Crystallogr. 1997, 30: 565