Nanocrystalline TiO2 as an efficient and reusable catalyst for the one-pot synthesis of polyhydroquinolien derivatives via Hantzsch reaction

Authors

Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.

Abstract

An efficient synthesis of polyhydroquinoline derivatives was reported via four-component coupling reactions of aldehydes, 1,3-dicarbonyl ketones (dimedone or 1,3-cyclohexanedione), ethyl acetoacetate or methyl acetoacetate and ammonium acetate in the presence of a catalytic amount of nanocrystalline TiO2 under solvent free conditions. The reported method is mild, rapid and has the advantages such as heterogeneous catalysis, simple work-up procedure, recyclability of the catalyst and purification of products without chromatographic methods.

Keywords


[1] F. Bossert, H. Meyer, E. Wehinger, Angew. Chem., Int. Ed.Engl. 20 (1981) 762–769.
[2] H. Nakayama, Y. Kasoaka, Heterocycles 42 (1996) 901–909.
[3] F. R. Buhler, W. J Kiowski, Hypertens. 5 (1987) S3-10.
[4] J. L. Reid, P. A. Meredith, F. Pasanisi, J. Cardiovasc. Pharmacol. 7 (1985) 18-20.
[5] V. Klusa, Drugs Future 20 (1995) 135–138.
[6] R. G. Bretzel, C. C. Bollen, E. Maester, K. F. Federlin, Am. J. Kidney. Dis. 21 (1993) 54–63.
[7] R. G. Bretzel, C. C. Bollen, E. Maester, K. F. Federlin, Drugs Future 17 (1992) 465–468.
[8] R. Boer, V. Gekeler, Drugs Future 20 (1995) 499–509.
[9] M. Li, Z. Zuo, L. Wen, S. J. Wang,  J. Comb. Chem. 10 (2008) 436-441.
[10] S. J. Tu, J. F. Zhou, X. Deng, P.J. Cai, H. Wang, J. C. Feng, Chin. J. Org. Chem. 21 (2001) 313-316.
[11] S. J. Jiang, Z. Q. Lu, J. Loa, T. P. Synlett (2004) 831-835.
[12] X. Y. Zhang, Y. Z. Li, X. S. Fan, G. R. Qu,X. Y. Hu, J. J. Wang, Chin. Chem. Lett. 17 (2006) 150-152.
[13] N. Tewari, N. Dwivedi, R. P. Tripathi, Tetrahedron Lett. 45 (2004) 9011–9014.
[14] G. V. M. Sharma, K. L. Reddy,P. S. Lakshmi, P. R. Krishna, Synthesis (2006) 55–58.
[15] M. M. Heravi, K. Bakhtiari, N. M. Javadi, F. F. Bamoharram, M. Saeedi, H. O. Oskooie, J. Mol. Catal. A: Chem. 264 (2007) 50–52.
[16] S. Ko, M. N. V. Sastry, C. Lin, C. F. Yao, Tetrahedron Lett. 46 (2005) 5771–5774.
[17] M. Maheswara,V. Siddaiah, Y. K. Rao, Y. M. Tzeng, C. Sridhar, J. Mol. Catal. A: Chem. 260 (2006)  179–180.
[18] R. Gupta, S. Paul, A. Loupy, Synthesis (2007) 2835–2838.
[19] M. Maheswara, V. Siddaiah, G. L. Damu, C. Venkata Rao, Arkivoc 2 (2006) 201-206.
[20] M. Z. Kassaee, M. Masrouri, F. Movahedi, Monatsch. Chem. 14 (2010) 317-322.
[21] J. L. Donelson, R. A. Gibbs, S. K. De, J. Mol. Catal. A: Chem. 256 (2006) 309-311.
[22] B. Das, B. Ravikanth, R. Ramu, B. Vittal Rao, Chem. Pharm. Bull. 54 (2006) 1044-1045.
[24] S. R. Cherkupally, R. Mekalan, Chem. Pharm. Bull. 56 (2008) 1002-1004.
[25] S. Kumar, P. Sharma, K. K. Kapoor, M. S. Hundal, Tetrahedron 64 (2008) 536-542.
[26] K. A. Undale, T. S. Shaikh, D. S. Gaikwad, D. M. Pore, C. R. Chimie 14 (2011) 511–515.
[27] D. M. Antonelli, Y. J. Ying, Angew. Chem. Int. Ed. Engl. 34 (1995) 2014-2017.
[28] D. M. Antonelli, Microporous Mesoporous Mater. 30 (1999) 315-319.
[29] F. Shirini, M. Alipour Khoshdel, M. Abedini, S. V. Atghia, Chin. Chem. Lett. 22 (2011) 1211–1214.
[30] M. Lakshmi Kantam, S. Laha, J. Yadav, B. Sreedhar, Tetrahedron Lett. 47 (2006) 6213-6216.
[31] M. Hosseini-Sarvari, Acta. Chim. Slov. 54 (2007) 354-359.
[32] M. Z. Kassaee, R. Mohammadi, H. Masrouri, F. Movahedi, Chin. Chem. Lett. 22 (2011) 1203-1206.
[33] J. L. Ropero-Vega, A. Aldana-Péreza, R. Gómez, M. E. Nino-Gómez, Appl. Catal. A: Gen. 379 (2010) 24–29.
[34] F. Shirini , M. Mamaghani, S. V. Atghia, Catal.Commun. 12 (2011) 1088–1094.