Chloroacetic acid-promoted heterocyclic reactions: Efficient preparation of tetrahydropyridines and 2,3-dihydroquinazolin-4(1H)-ones

Subject Areas : Iranian Journal of Catalysis

Malek Taher Maghsoodlou ¹ , Nourallah Hazeri ² , Elham Fereidooni ³ , Sajjad Salahi ⁴ , Nasrin Mahmoudabadi ⁵ , Naeime Khorshidi ⁶ , Jasem Aboonajmi ⁷ , Mojtaba Lashakri ⁸

1 - Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran.
2 - Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
3 - Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
4 - Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
5 - Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
6 - Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
7 - Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
8 - Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran

Received: 2014-10-20 Accepted : 2015-01-15 Published : 2015-09-01

Keywords:

References:

[1] A. Dömling, Chem. Rev. 106 (2006) 17-89.
[2] C. Hulme, V. Gore, Curr. Med. Chem. 10 (2003) 51-80.
[3] J. Zhu, Eur. J. Org. Chem. (2003) 1133-1144.
[4] T. Ngouansavanh, J. Zhu, Angew. Chem. Int. Ed. 46 (2007) 5775-5778.
[5] E.K. Laurent, M. Gizolme, L. Grimaud, J. Oble, Org. Lett. 8 (2006) 4019-4021.
[6] B.M. Trost. Angew. Chem. Int. Ed. Engl. 34 (1995) 259-281.
[7] L. Weber, Curr. Med. Chem. 9 (2002) 2085-2093.
[8] M. Dabiri, P. Salehi, M. Baghbanzadeh, Monatsh. Chem. 138 (2007) 1191-1194.
[9] M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, Doostmohamadi, R. Synth. Commun. 43 (2013) 635-644.
[10] A.T. Khan, M.M. Khan, K.K.R. Bannuru, Tetrahedron 66 (2010) 7762-7772.
[11] A.T. Khan, T. Parvin, and L.H. Choudhury, J. Org. Chem. 73 (2008) 8398-8402.
[12] H.-J. Wang, L.-P. Mo, and Z.-H. Zhang, ACS Comb. Sci. 13 (2011) 181-185.
[13] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.J. Shams-Najafi, Monatsh. Chem. 143 (2012) 939-945.
[14] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, A.C. Willis, Chin. Chem. Lett. 23 (2012) 569-572.
[15] V.B. Rao, C.V. Ratnam, Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem. 18 (1979) 409-412.
[16] CAS No. 63384-42-9. Spectral data compared with that obtained from WSS; Wiley Subscription Services, Inc., US.
[17] M. Baghbanzadeh, P. Salehi, M. Dabiri, G. Kozehgary, Synthesis 2 (2006) 344-348.
[18] G.P. Cai, X. L. Xu, Z. F. Li, W. P. Weber, and P. Lu, J. Heterocycl. Chem. 39 (2002) 1271-1272.
[19] J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su, Tetrahedron Lett. 49 (2008) 3814-3818.
[20] M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgary, A.A. Mohammadi, Tetrahedron Lett. 46 (2005) 6123-6126.
[21] M. Wang, J.J. Gao, Z.G. Song, L. Wang, Chem. Heterocycl. Comp. 47 (2011) 851-855.
[22] R.Z. Qiao, B.L. Xu, Y.H. Wang, Chin. Chem. Lett. 18 (2007) 656-658.
[23] S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, H. Sepehrian, S. Ebrahimi, Synthesis 8 (2010) 1356-
1360.
[24] H.R. Shaterian, A.R. Oveisi, Chin. J. Chem. 27 (2009) 2418-2422.