SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 4: 761 - 766

DOI: https://doi.org/10.6023/cjoc201310038

A Novel and Green Method for the Synthesis of 4-Thiazolidinones with the Sources of 2-Chloroacetamide and Thioureas

  • Zhao Huarong ,
  • Wang Ling ,
  • Wang Yudan
Expand
  • a Department of Chemistry, Zhejiang University, Hangzhou 310027;
    b College of Chemistry & Chemical Engineering, Shaoxing University, Shaoxing 312000

Received date: 2013-10-25

  Revised date: 2013-12-05

  Online published: 2013-12-19

Supported by

Project supported by the Natural Science Foundation of Zhejiang Province (Nos. LY12B02015, Y4080234).

Fold

Abstract

A novel, green synthetic method for 4-thiazolidinones in the ionic liquids was reported. 4-Thiazolidinones were prepared with the sources of substituted thioureas and 2-chloroacetamide in the ionic liquids. This method offers several advantages like high yield, short reaction time and mild reaction conditions. The reaction mechanism was studied and the result showed that ammonia was removed in the reaction, which was the first reported.

Key words： 4-thiazolidinones; 2-chloroacetamide; ionic liquid; mechanism; green

Cite this article

Zhao Huarong , Wang Ling , Wang Yudan . A Novel and Green Method for the Synthesis of 4-Thiazolidinones with the Sources of 2-Chloroacetamide and Thioureas[J]. Chinese Journal of Organic Chemistry, 2014 , 34(4) : 761 -766 . DOI: 10.6023/cjoc201310038

References

[1] Bonde, C. G.; Gaikwad, N. J. Bioorg. Med. Chem. 2004, 12, 2151.
[2] Amin, K. M.; Rahman, D. E. A.; Al-Eryani, Y. A. Bioorg. Med. Chem. 2008, 16, 5377.
[3] Havrylyuk, D.; Mosula, L.; Zimemkovsky, B.; Vasylenko, O.; Gzella, A.; Lesyk, R. Eur. J. Med. Chem. 2010, 45, 5012.
[4] Zhang, D.-Y.; Xiang, H.; Xu, Y.-G.; Hua, W.-Y. Acta Pharm. Sin. 2006, 41, 825 (in Chinese).(张大永, 向华, 徐云根, 华维一, 药学学报, 2006, 41, 825.)
[5] Unangst, P. C.; Connor, D. T.; Cetenko, W. A.; Sorenson, R. J.; Kostlan, C. R.; Sircar, J. C.; Wright, C. D.; Schrier, D. J.; Dyer, R. D. J. Med. Chem. 1994, 37, 322.
[6] Dixit, N.; Salvi, V. K.; Talesara, G. L. Int. J. Chem. Sci. 2005, 3, 31.
[7] Urbano, M.; Guerrero, M.; Velaparthi, S.; Crisp, M.; Chase, P.; Hodder, P.; Schaeffer, M. T.; Brown, S.; Rosen, H.; Roberts, E. Bioorg. Med. Chem. Lett. 2011, 21, 6739.
[8] Bahekar, S. S.; Shinde, D. B. J. Korean Chem. Soc. 2003, 47, 237.
[9] Rahnema, M.; Bigdell, M. R.; Kazemizadeh, A. R.; Ramazani, A. Phosphorus, Sulfur Silicon Related. Elem. 2007, 182, 1683.
[10] Bose, A. K.; Spiegeiman, G.; Manhas, M. S. J. Am. Chem. Soc. 1968, 90, 4508.
[11] Meng, X.-W.; Lu, F.-P.; Zhao, H.-R. Acta Chim. Sinica 2011, 69, 2281 (in Chinese).(孟祥武, 陆丰平, 赵华绒, 化学学报, 2011, 69, 2281.)
[12] Ghorab, M. M.; Shaaban, M. A.; Refaat, H. M.; Heiba, H. I.; Ibrahim, S. S. Eur. J. Med. Chem. 2012, 53, 403.
[13] Zhang, M.-M.; Zhou, Y.-J.; Li, Y.-L.; Liu, Y.; Wang, X.-S. Chin. J. Org. Chem. 2013, 33, 1728 (in Chinese).(张梅梅, 周玉静, 李玉玲, 刘蕴, 王香善, 有机化学, 2013, 33, 1728.)
[14] Dong, T.-W.; Zhou, P.-L.; Jing, G.-B.; Wu, G.-X.; Jia, Y.-Y. J. Fudan Univ. (Nat. Sci.) 1993, 32, 287 (in Chinese).(董庭威, 周鹏麟, 金关宝, 伍国贤, 贾韵仪, 复旦学报(自然科学版), 1993, 32, 287.)
[15] Peng, Y.-Q.; Song, G.-H.; Liu, L. Org. Prep. Proced Int. 2004, 36, 151.
[16] Saeed, A.; Abbas, N.; Flörke, U. J. Braz. Chem. Soc. 2007, 18, 559.
[17] Roland, P. F.; Schroepl, E. Pharmazie 1968, 23, 561.
[18] Bhaskar, D.; Rout, M. V. J. Sci. Ind. Res. 1955, 14B, 16.
[19] Vasa, M. L.; Trivedi, J. J.; Kshatriya, K. C. J. Indian Chem. Soc. 1959, 36, 648.
[20] Mahboobi, S.; Sellmer, A.; Hocher, H.; Eichhorn, E.; Bär, T.; Schmidt, M.; Maier, T.; Stadlwieser, J. F.; Beckers, T. L. J. Med. Chem. 2006, 49, 5769. Mahapatra, G. N.; Rout, M. K. J. Indian Chem. Soc. 1956, 33, 17.
Options
Outlines

/

〈 〉