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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;
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Publication History

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

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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.

Key words

green method - synthesis - thiazolidine-2-thione - MCR - heterocyclic compounds

    References and Notes

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