Nanocrystalline MgAl2O4 as a Heterogeneous Nanocatalyst for the Synthesis of 2-Ketomethylquinolines Using Green Design Methodology

Document Type : Research Paper

Authors

Laboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R., Iran.

10.7508/jns.2013.02.007

Abstract

In this investigation, a facile and green sonochemical route has been developed for the synthesis of 2-Ketomethylquinolines by using 2-methylquinolines and several acyl chlorides in the presence of nanocrystalline MgAl2O4 as an efficient heterogeneous catalyst. The combination of nanocatalyst and ultrasonic process afforded corresponding ketomethyl quinolines in shorter reaction durations, and in high yields. This work consistently has the advantages of excellent yields, short reaction time, mild condition and work-up procedures. This method might be useful in the future for the preparation of similar derivatives.

Keywords

References

[1] M. Nasrollahzadeh, A. Ehsani, A. Rostami-Vartouni, Ultrason Sonochem. 21 (2014) 275-282.
[2] M. Salavati-Niasari, Inorg. Chim. Acta. 362 (2009) 2159-2166.
[3] (a) M. B. Gawande, R. K. Pandey and R. V. Jayaram, Catal. Sci. Technol. 2 (2012) 1113-1125; (b) A. Corma, J. Catal. 216 (2003) 298-312; (c) M. R. Othman, Z. Helwani, Martunus and W. J. N. Fernando, Appl. Org. Chem. 23 (2009) 335-346; (d) S. M. Mahajani and M. M. Sharma, Org. Process Res. Dev. 1 (1997) 97-105; (e) L. Delaude, P. Laszlo and K. Smith, Acc. Chem. Res. 26 (1993) 607-613; ( f) M. B. Gawande, V. Polshettwar, R. S. Varma and R. V. Jayaram, Tetrahedron Lett. 48 (2008) 8170-8173.
[4] M. B. Gawande, P. S. Brancoa, R. S. Varma, Chem. Soc. Rev. 42 (2013) 3371-3393.
[5] J. Safari, S. Gandomi-Ravandi, Z. Akbari, Journal of Advanced Research. (2012) http://dx.doi.org/10.1016/j.jare.2012.09.001.
[6] J. Ahmad, M. E. Mazhar, M. Q. Awan, M. N. Ashiq, Physica B. 406 (2011) 3484-3488.
[7] E. Navaei Alver, M. Rezaei, H. Navaei Alver, Powder Technol. 198 (2010) 275-278.
[8] H. Loghmani-Khouzani, R. Gawinecki, M. M. Sadeghi, H. Mehrabi, B. Osmailowski, J. Iran. Chem. Soc. 2 (2005) 294-299.
[9] J. V. Greenhill, H. Loghmani-Khouzani, Spectrochim. Acta, Part A. 46 (1990) 803-808.
[10] H. Loghmani-Khouzani, H. Sabzyan, A Rezaei-Pooranari, Dyes and Pigments. 76 (2006) 447-454.
[11] J. Safari, M. Adib, F. Sheibani, Z. Sadeghi, Turk J Chem. 30 (2006) 673-679.
[12] A. E. M. Saeed, S. A. Elhadi, Synthetic Commu. 41 (2011) 1435-1443.
[13] E. S. H. El Ashry, A. A. Kassem, E. Ramadan, Adv. Heterocycl. Chem. 90 (2006) 1-123.
[14] R. Roussel, M. O. de Guerrero, J. C. Galin, Macromolecules. 19 (1986) 291-299.
[15] H. Loghmani-Khouzani,; H.Minaeifar; R. Gawinecki, J. Mol. Struct. 1032 (2013) 138-146.
[16] (a) J. Wang, Y. Zong, R. Fu, Y. Niu, G. Yue, Z. Quan, X. Wang, Y. Pan, Ultrason Sonochem. 21 (2011) 29-34; (b) J. T. Li, M. X. Sun, Y. Yin, Ultrason. Sonochem. 17 (2010) 359-362; (c) A. Bazgir, S. Ahadi, R. Ghahremanzadeh, H. R. Khavasi, P. Mirzaei, Ultrason. Sonochem. 17 (2010) 447-452.
[17] H. Loghmani-Khouzani, M. M. Sadeghi, J. Safari, A. Minaeifar, Tetrahedron Lett. 42 (2001) 4363-4364.
[18] D. Nagargoje, P. Mandhane, S. Shingote, P. Badadhe ,C. Gill, Ultrason. Sonochem. 19 (2012) 94-96.
[19] S. Sadjadi, H. Sepehrian, Ultrason Sonochem. 18 (2011) 480-483.
[20] D. N. Zhang, J.T. Li, Y.L. Song, H.M. Liu, H.Y. Li, Ultrason. Sonochem. 19 (2012) 475-478.
[21] E. Kolehmainen, B. Osmiałowski, T.M. Krygowski, R. Kauppinen, M. Nissinen, R. Gawinecki, J Chem Soc Perk T1. 2 (2000) 1259-1266.
[22] J. V. Greenhill, H. Loghmani-Khouzani, D. J. Maitland, J Chem Soc Perk T1. 1 (1991) 2831-2840.
[23] R. Gawinecki, B. Osmiałowski, E. Kolehmainen, M. Nissinen, J Mol Struct. 525 (2000) 233-239.
 

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