An Efficient Method for Synthesis of Thiohydantoins with a-Amino Esters Under Microwave Irradiation

Yanmei Zhao; Zhouyu Wang; Zhenju Jiang; Hualin Feng; Li Liu; Ju Wang

doi:10.14233/ajchem.2014.16119

Issue

Vol. 26 No. 4 (2014): Vol 26 Issue 4

Issue Published : February 15, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

An Efficient Method for Synthesis of Thiohydantoins with a-Amino Esters Under Microwave Irradiation

https://doi.org/10.14233/ajchem.2014.16119

Yanmei Zhao

Department of Pharmaceutics Engineering, Xihua University, Chengdu, 610039, P.R. China

Zhouyu Wang

Department of Pharmaceutics Engineering, Xihua University, Chengdu, 610039, P.R. China

Zhenju Jiang

Department of Pharmaceutics Engineering, Xihua University, Chengdu, 610039, P.R. China

Hualin Feng

Department of Pharmaceutics Engineering, Xihua University, Chengdu, 610039, P.R. China

Li Liu

Department of Pharmaceutics Engineering, Xihua University, Chengdu, 610039, P.R. China

Ju Wang

Department of Pharmaceutics Engineering, Xihua University, Chengdu, 610039, P.R. China

Corresponding Author(s) : Zhouyu Wang

zhouyuwang@mail.xhu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 4 (2014): Vol 26 Issue 4
Article Published : February 15, 2014

Abstract

An efficient and simple way for synthesis of thiohydantoins is reported. In the absence of any additional catalysts, a series of thiohydantoins were synthesized with amino esters and isothiocyanates in aqueous medium under microwave irradiation. Excellent isolated yields (up to 98 %) were obtained under mild conditions.

Keywords

Thiohydantoin Microwave irradiation Amino esters Isothiocyanates

Zhao, Y., Wang, Z., Jiang, Z., Feng, H., Liu, L., & Wang, J. (2014). An Efficient Method for Synthesis of Thiohydantoins with a-Amino Esters Under Microwave Irradiation. Asian Journal of Chemistry, 26(4), 1171–1173. https://doi.org/10.14233/ajchem.2014.16119

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P. Edman, Acta Chem. Scand., 4, 283 (1950); doi:10.3891/acta.chem.scand.04-0283.

R. Kumar, S. Khan and P. M.S. Chauhan, Curr. Drug Targets, 12, 1689 (2011); doi:10.2174/138945011798109428.

A.A. El-Barbary, A.I. Khodair, E.B. Pedersen and C.J. Nielsen, Med. Chem., 37, 73 (1994); doi:10.1021/jm00027a009.

B. Mo, J. Li and S. Liang, Anal. Biochem., 249, 207 (1997); doi:10.1006/abio.1997.2156.

E. Osz, L. Somsak, L. Szilagyi, L. Kovacs, T. Docsa, B. Toth and P. Gergely, Bioorg. Med. Chem. Lett., 9, 1385 (1999); doi:10.1016/S0960-894X(99)00192-4.

R. Kuang, J.B. Epp, S. Ruan, H. Yu, P. Huang, S. He, J. Tu, N.M. Schechter, J. Turbov, C.J. Froelich and W.C. Groutas, J. Am. Chem. Soc., 121, 8128 (1999); doi:10.1021/ja990160e.

T.-S. Lee, L.-C. Chen, Y. Liu, J. Wu, Y.-C. Liang and W.-S. Lee, Naunyn Schmiedebergs Arch. Pharmacol., 382, 43 (2010); doi:10.1007/s00210-010-0519-4.

M.E. Jung, S. Ouk, D. Yoo, C.L. Sawyers, C. Chen, C. Tran and J. Wongvipat, J. Med. Chem., 53, 2779 (2010); doi:10.1021/jm901488g.

M. Ono, S. Hayashi, K. Matsumura, H. Kimura, Y. Okamoto, M. Ihara, R. Takahashi, H. Mori and H. Saji, ACS Chem. Neurosci, 2, 269 (2011); doi:10.1021/cn200002t.

J. Han, H. Dong, Z. Xu, J. Lei and M. Wang, Int. J. Mol. Sci., 14, 12484 (2013); doi:10.3390/ijms140612484.

N. Hussain, A. Joshi, C. Sharma and G. L. Talesara, Asian J. Chem., 24, 5917 (2012).

D.S. Raghuvanshi and K.N. Singh, Phosphorus Sulfur Silicon Rel. Elem., 185, 2243 (2010); doi:10.1080/10426500903567554.

C. Yao, Y. Zhang, G. Zhang, W. Chen, Y. Yu and R.A. Houghten, Synth. Commun., 40, 717 (2010); doi:10.1080/00397910903013697.

M. Carboni, J.-M. Gomis, O. Loreau and F. Taran, Synthesis, 417 (2008); doi: 10.1055/s-2008-1032024.

S. Cao, L.J. Zhu, C.M. Zhao, X.H. Tang, H.J. Sun, X. Feng and X.H. Qian, Monatsh. Chem., 139, 923 (2008); doi:10.1007/s00706-007-0842-8.

G.S.M. Sundaram, C. Venkatesh, H. Ila and H. Junjappa, Synlett, 251 (2007); doi: 10.1055/s-2007-967987.

Z.D. Wang, S.O. Sheikh and Y. Zhang, Molecules, 11, 739 (2006); doi:10.3390/11100739.

S. Reyes and K. Burgess, J. Org. Chem., 71, 2507 (2006); doi:10.1021/jo052576i.

S. Porwal, R. Kumar, P.R. Maulik and P.M.S. Chauhan, Tetrahedron Lett., 47, 5863 (2006); doi:10.1016/j.tetlet.2006.06.076.

J.P. Li, C.M. Ma and G.R. Qu, Synth. Commun., 35, 1203 (2005); doi:10.1081/SCC-200054778.

J. Li, Z. Wang, Z. Jiang, S. Jiang and L. Xiong, Asian J. Chem., 23, 4101 (2011).

S. Jiang, Z. Wang, Z. Jiang, J. Li, S. Zhou and L. Pu, Lett. Org. Chem., 9, 24 (2012); doi:10.2174/157017812799304006.

S. Caddick and R. Fitzmaurice, Tetrahedron, 65, 3325 (2009); doi:10.1016/j.tet.2009.01.105.

H.M. Hugel, Molecules, 14, 4936 (2009).

E. Guenin and D. Meziane, Curr. Org. Chem., 15, 3465 (2011); doi:10.2174/138527211797374724.

G.K. Gupta, N. Rani and V. Kumar, Mini Rev. Org. Chem., 9, 270 (2012); doi:10.2174/1570193X11209030270.

Issue

Vol. 26 No. 4 (2014): Vol 26 Issue 4

An Efficient Method for Synthesis of Thiohydantoins with a-Amino Esters Under Microwave Irradiation

Corresponding Author(s) : Zhouyu Wang

Abstract

Keywords

Full Article

Download Citation

References

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