Synlett 2010(6): 973-975  
DOI: 10.1055/s-0029-1219558
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Water-Mediated Multicomponent Reaction: A Facile and Efficient Synthesis of Multisubstituted Thiazolidine-2-thiones

Shi-Feng Gan, Jie-Ping Wan, Yuan-Jiang Pan, Cui-Rong Sun*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87951629; e-Mail: suncuirong@zju.edu.cn;
Further Information

Publication History

Received 1 December 2009
Publication Date:
02 March 2010 (online)

Abstract

A facile, efficient, and green method for the synthesis of multisubstituted thiazolidine-2-thione derivatives via a three-component reaction of amine, carbon disulfide, and α-bromoketone is described. By using water as the reaction medium, the reaction proceeds smoothly to give corresponding products in good to excellent yields.

    References and Notes

  • 1a Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
  • 1b Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res.  2003,  36:  899 
  • 1c Zhu J. Eur. J. Org. Chem.  2003,  1133 
  • 1d Pinto A. Neuville L. Zhu J. Angew. Chem. Int. Ed.  2007,  46:  3291 
  • 2a Nagao Y. Miyasaka T. Seno K. Fujita E. J. Chem. Soc., Perkin Trans. 1  1984,  2439 
  • 2b Singh R. Dikshit SK. Polyhedron  1995,  14:  1799 
  • 2c Garraway JL. J. Chem. Soc. B  1966,  92 
  • 2d Chanon F. Rajzmann M. Chanon M. Metzger J. Pouzard G. Drakenberg T. Can. J. Chem.  1980,  58:  604 
  • 2e Roux MV. Temprado M. Jiménez P. Foces-Foces C. Notario R. Parameswar AR. Demchenko AV. Chickos JS. Deakyne CA. Ludden AK. Liebman JF. J. Phys. Chem. A  2009,  113:  10772 
  • 3 Tao L. Liu J. Xu J. Davis TP. Org. Biomol. Chem.  2009,  7:  3481 
  • 4 Šubr V. Ulbrich K. React. Funct. Polym.  2006,  66:  1525 
  • 5a Bell NA. Clegg W. Coles SJ. Constable CP. Harrington RW. Hursthouse MB. Light ME. Raper ES. Sammon C. Walker MR. Inorg. Chim. Acta  2004,  357:  2091 
  • 5b Wei X. Chu W. Huang R. Zhang S. Li H. Zhu Q. Inorg. Chem. Commun.  2006,  9:  1161 
  • 5c Aznárez J. Castillo JR. Luesma C. Analyst  1981,  106:  1122 
  • 5d Wei X. Di D. Chu W. Zhu Q. Huang R. Inorg. Chim. Acta  2008,  361:  1819 
  • 6a Lamon RW. Humphlett WJ. Blum WP.
    J. Heterocycl. Chem.  1967,  4:  349 
  • 6b Ege G. Arnold P. Noronha R. Liebigs Ann. Chem.  1979,  656 
  • 6c D’Amico JJ. Bollinger FG. Freeman JJ. Dahl WE. J. Heterocycl. Chem.  1986,  23:  105 
  • 7 Humphlett WJ. Lamon RW. J. Org. Chem.  1964,  29:  2146 
  • 8 Sudo A. Morioka Y. Koizumi E. Sanda F. Endo T. Tetrahedron Lett.  2003,  44:  7889 
  • 9 Foglia TA. Gregory LM. Maerker G. Osman SF. J. Org. Chem.  1971,  36:  1068 
  • 10 Ge Z. Cui J. Wang Y. Cheng T. Li R. Synthesis  2004,  1257 
  • 11a Alizadeh A. Rostamnia S. Zohreh N. Hosseinpour R. Tetrahedron Lett.  2009,  50:  1533 
  • 11b Azizi N. Aryanasab F. Torkiyan L. Ziyaei A. Saidi MR. J. Org. Chem.  2006,  71:  3634 
  • 11c Azizi N. Torkiyan L. Saidi MR. Org. Lett.  2006,  8:  2079 
  • 12 Wan J. Gan S. Wu J. Pan Y. Green Chem.  2009,  11:  1633 
13

Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 747685.

14

General Procedure
To a solution of amines 1 (0.75 mmol) in H2O (3 mL), CS2 (1.5 mmol) and α-bromoketone 2 (0.5 mmol) were added. Subsequently, K2CO3 (0.25 mmol) was located to the mixture. After stirring the mixture at r.t. for 1 h, the mixture was extracted with EtOAc (3 × 10 mL), and the combined organic layers were dried overnight with anhyd Na2SO4. After the organic solvent was removed, the residue was subjected to silical gel chromatography PE-EtOAc (5:1) as eluent to give pure products.