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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 9: 1895 - 1899

DOI: https://doi.org/10.6023/cjoc201404009

An Efficient Synthesis of 2,3-Dihydrothiophene Derivatives from Four-Component Reactions under Catalyst-Free Conditions

  • Zhang Jinpeng ,
  • Gao Yanian ,
  • Chen Ming ,
  • Jiang Ling ,
  • Xia Sheng ,
  • Rong Liangce
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  • a School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116;
    b Department of Public Health, Xuzhou Medical College, Xuzhou 221004

Received date: 2014-04-03

  Revised date: 2014-04-29

  Online published: 2014-05-07

Supported by

Project supported by the National Natural Science Foundation of China (No. 21172188), and the Open Foundation of Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials (No. K201312).

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Abstract

An efficient synthesis of 2,3-dihydrothiophene derivatives by the four-component reactions of aromatic aldehydes, thiazolidine-2,4-dione, malononitrile and pyridin-3-ylmethanamine has been reported. This reaction could be carried out smoothly without using any other catalysts in ethanol (95%) and the aromatic heterocyclic amine (pyridin-3-ylmethanamine) was first used for the synthesis of 2,3-dihydrothiophene derivatives. The advantages of this procure were mild reaction conditions, easy operation, and high yields. The products were identified by IR, 1H NMR and HRMS.

Key words： thiophene; thiazolidine-2,4-dione; pyridin-3-ylmethanamine; four-component reactions

Cite this article

Zhang Jinpeng , Gao Yanian , Chen Ming , Jiang Ling , Xia Sheng , Rong Liangce . An Efficient Synthesis of 2,3-Dihydrothiophene Derivatives from Four-Component Reactions under Catalyst-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2014 , 34(9) : 1895 -1899 . DOI: 10.6023/cjoc201404009

References

[1] Sperry Jeffrey, B.; Wright, D.L.Curr.Opin.Drug Discovery Dev.2005, 8, 723.
[2] Wu, C.; Decker, E.R.; Blok, N.; Bui, H.; You, T.J.; Wang, J.; Bourgoyne, A.R.; Knowles, V.; Berens, K.L.; Holland, G.W.; Brock, T.A.; Dixon, R.A.F.J.Med.Chem.2004, 47, 1969.
[3] Gewald, K.Angew.Chem.1961, 73, 114.
[4] Chakrabarti, J.K.; Hotten, T.M.; Tupper, D.E.Preparation of 2-Methylthienobenzodiazepine as Central Nervous System Agent (Lilly Industries Ltd., UK), Application, US, 11 pp, Cont-in-part of US Ser No 44, 844, abandoned.1997.
[5] Sun, J.; Zhang, L.L.; Xia, E.Y.; Yan, C.G.J.Org.Chem.2009, 74, 3398.
[6] Lu, G.P.; Zeng, L.Y.; Cai, C.Green Chem.2011, 13, 998.
[7] Tong, D.; Xia, S.; Tao, S.M.; Gao, L.J.; Feng, Y.J.; Rong, L.C.Res.Chem.Intermed.2013, 39, 561.
[8] Sun, J.; Xia, E.Y.; Yao, R.; Yan, C.G.Mol.Diversity 2011, 15, 115.
[9] Sun, J.; Wu, Q.; Xia, E.Y.; Yan, C.G.Synthesis 2010, 3987.
[10] Gao, L.J.; Xia, S.; Wu, N.; Tao, S.M.; Feng, Y.J.; Rong, L.C.Synth.Commun.2013, 43, 2590.
[11] Shi, D.Q.; Zou, Y.; Hu, Y.; Wu, H.J.Heterocycl.Chem.2011, 48, 896.

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