Green and one-pot synthesis of tetrahydropyridine derivatives using tetramethylguanidinium acetate as a reusable ionic liquid catalyst

Document Type : Original Article

Author

Abstract

A simple and efficient method has been presented for the synthesis of tetrahydropyridine derivatives via one-pot reaction of aromatic amines (2 eqv), β-ketoesters (1 eqv) and aromatic aldehydes (2 eqv) in the presence of N,N,N′,N′-tetramethylguanidinium acetate [TMG][Ac]. The reaction was carried out in EtOH under reflux conditions. Some of the advantages of this procedure are green and safe solvent, high atom economy, high yield, and no need to column chromatography for product purification. Moreover, the catalyst is recyclable and can be used up to four times without significant loss of its activity.

Keywords

References

[1] کوکبی، نادیا؛ اتوکش، سمیه؛ عموزاده، علی؛ کلوری، اسکندر؛ مجله شیمی کاربردی دانشگاه سمنان، شماره 31 (1393) ص 31.
[2] حسن‌پور، اکبر؛ حسین‌زاده خانمیری، رحیم؛ قربانپور، خاطره؛ ابوالحسنی، جعفر؛ موسائی اسکوئی، یونس؛ مجله شیمی کاربردی دانشگاه سمنان، شماره 33 (1393) ص 51.
[3] M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem., 17 (2009) 625.
[4] S. Petit, J.P. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, J.L. Imbs, Eur. J. Med. Chem., 26 (1991) 19.
[5] Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, S.E. Webber, T. Hermann, D. Wall, Bioorg. Med. Chem. Lett., 17 (2007) 1206.
[6] B. Ho, A.M. Grider, J.P. Stables, Eur. J. Med. Chem., 36 (2001) 265.
[7] H. Sun, D.O. Scott, ACS Med. Chem. Lett., 2 (2011) 638.
[8] P.A. Clark, A.V. Zaytzev, A.C. Whitwood, Tetrahedron Lett., 48 (2007) 5209.
[9] A.T. Khan, T. Parvin, L.H. Choudhury, J. Org. Chem., 73 (2008) 8398.
[10] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, A.C. Willis, Chin. Chem. Lett., 23 (2012) 569.
[11] A.T. Khan, Md.M. Khan, K.K.R. Bannuru, Tetrahedron, 66 (2010) 7762.
[12] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, A.C. Willis, J. Iran. Chem. Soc., 10 (2013) 863.
[13] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, M. Lashkari, J. Chem. Res., 36 (2012) 463.
[14] H.-J. Wang, L.-P. Mo, Z.-H. Zhang, ACS Comb. Sci., 13 (2011) 181.
[15] M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, R. Doostmohamadi, Synth. Commun., 43 (2013) 635.
[16] S. Mishra, R. Ghosh, Tetrahedron Lett., 52 (2011) 2857.
[17] R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron, 68 (2012) 363.
[18] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.J. Shams-Najafi, Monatsh. Chem., 143 (2012) 939.
[19] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A.C. Willis, Res. Chem. Intermed., 40 (2014) 723.
[20] M.G. Afkham, A. Elhampour, F. Nemati, J. Appl. Chem., 10 (2016) 55.
[21] B. Barfi, A. Asghari, M. Rajabi, J. Appl. Chem., 8 (2014) 51.
[22] E. Ghobadi, M. Peiravi, E. Kolvari, J. Appl. Chem., 10 (2016) 49.
[23] S.S. Sajadikhah, M.T. Maghsoodlou, RSC. Adv., 4 (2014) 43454.
[24] M. Doble, A. Kumar, Green Chemistry and Engineering, Elsevier (2007).
[25] H. Veisi, A.A. Manesh, N. Khankhani, R. Ghorbani-Vaghei, RSC Adv., 4 (2014) 25057.
[26] D.L. Pavia, G.M. Lampman, G.S. Kriz, J.R. Vyvyan, Introduction to Spectroscopy, 4th ed., Brooks/Cole: Belmont, CA (2009).
Applied Chemistry Today
Volume 12, Issue 43
June 2017
Pages 23-32

Files

Share

How to cite

Statistics