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

محورهای موضوعی : Iranian Journal of Catalysis

Malek Taher Maghsoodlou ¹ (Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran.)
Nourallah Hazeri ² (Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Elham Fereidooni ³ (Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Sajjad Salahi ⁴ (Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Nasrin Mahmoudabadi ⁵ (Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Naeime Khorshidi ⁶ (Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran)
Jasem Aboonajmi ⁷ (Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran)
Mojtaba Lashakri ⁸ (Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran)

تاریخ دریافت : 1393/07/28 تاریخ پذیرش : 1393/10/25 تاریخ انتشار : 1394/06/10

کلید واژه: Multi-component reaction, Tetrahydropyridines, Mild conditions, 2, 3-Dihydroquinazolin-4(1H)-ones,

چکیده مقاله :

Facile and versatile procedures have been explored for the synthesis of tetrahydropyridines and 2,3-dihydroquinazolin-4(1H)-ones. These protocols employ the one-pot multi-component condensation of arylaldehydes and aromatic amines with β-keto esters and isatoic anhydride in chloroacetic acid, respectively. The reactions proceeded smoothly to generate the corresponding products in high yield. We have found that the use of chloroacetic acid as catalyst results in a remarkable beneficial effect on the reaction, allowing it to be performed without the need of any co-catalyst, which is the case in other similar reported methodologies. In addition, the preparation of 2,3-dihydro-4(1H)-quinazolinones derivatives from the reaction of arylaldehydes and anthranilamide in the presence of mentioned catalyst is reported.

منابع و مأخذ:

[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.