LaCl3.7H20: An efficient catalyst for one-pot multi-component synthesis of 1,4-polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction

Document Type: Original Research Article

Authors

1 Research Centre and Post Graduate Department of Chemistry, PadmashriVikhePatil College of Arts, Science and Commerce Pravaranagar At./Po. Lonikd. Tal.Rahata. Dist. Ahmednagar. 413713. (MS). India. (Affiliated to SavitribaiPhule Pune University, Pune)

2 Applied Chemistry Division, DIAT-DRDO, Girinagar, Pune. 411025.(MS) India.

3 Research Centre and Post Graduate Department of Chemistry, PadmashriVikhe Patil College of Arts, Science and Commerce Pravaranagar At./Po. Lonikd. Tal.Rahata. Dist. Ahmednagar. 413713. (MS). India. (Affiliated to Savitribai Phule Pune University, Pune)

4 Research Centre and Post Graduate Department of Chemistry, Padmashri Vikhe Patil College of Arts, Science and Commerce Pravaranagar At./Po. Lonikd. Tal.Rahata. Dist. Ahmednagar. 413713. (MS). India. (Affiliated to Savitribai Phule Pune University, Pune)

5 Post Graduate and Research Centre, Department of Chemistry, Padmashri Vikhe Patil College of Arts, Science and Commerce Pravaranagar, (Loni kd) Tal. Rahata. Dist. Ahmednagar 413713 (MS) India.

Abstract

An efficient one pot multi component synthesis of 1, 4-Polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction using lanthanum chloride heptahydrate (LaCl3.7H2O) from an aromatic aldehyde, ethyl acetoacetate, dimedone and ammonium acetate as a nitrogen precursor in ethanol at room temperature is described. In the present work we report lanthanum chloride heptahydrate remarkably non-toxic in nature and ease of handling we explored the utility of lanthanum chloride as a catalyst for the synthesis of 1, 4-polyhydroquinoline derivatives. We newly report p-N, N-dimethylamino-cinnamaldehyde and m-chlorobenzaldehyde for the synthesis of 1, 4-Polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction and was characterized by IR and 1HNMR spectroscopic methods.

Graphical Abstract

LaCl3.7H20: An efficient catalyst for one-pot multi-component synthesis of 1,4-polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction

Keywords

Main Subjects


[1] (a) F. Bertozzi, M. Gustafsson and R. Olsson, Org. Lett., 2002, 4, 3147-3150. (b) B.M. Trost, Angew Chem. Int. Ed. Engl., 1995, 34, 259-281. (c) A. Domling and I. Ugi,  Angew. Chem. Int. Ed., 2000, 39, 3168-3210.

[2] M. Nikpassand, M. Mamaghani and K. Tabataba, Molecules, 2009, 14, 1468-1474.

[3] (a) R. Simsek, U.B. Ismailoglu, C. Safak and I. Sahin-Erdemli, Farmaco, 2000, 55, 665-668. (b) Y.L. Chen, K.C. Fang, J.Y. Sheu, S.L. Hsu and C.C. Tzeng, J. Med. Chem., 2001, 44, 2374-2377. (c) G. Roma, M.D. Braccio, G. Grossi and M. Chai, Eur. J. Med. Chem., 2000, 35, 1021-1035. (d) M.P. Maguire, K.R. Sheets, K. Mcvety, A.P. Spada and A. Ziberstein, J. Med. Chem., 1994, 37, 2129-2137.

[4] S. Ko, M.N.V. Sastry, C. Lin and C. Yao, Tett. Lett., 2005, 46, 5771-5774.

[5] G. Sabitha; G.S.K.K. Reddy, S. Ch. Reddy and J.S. Yadav, Tett. Lett., 2003, 44, 4129-4131.

[6] R. Sridhar and P.T. Perumal, Tetrahedron, 2005, 61, 2465-2470.

[7] B. Das, B. Ravikanth, R. Ramu, B.V. Rao, Chem. Pharm. Bull., 2006, 54, 1044-1045.

[8] S. Ko and C.F. Yao, Tetrahedron, 2006, 62, 7293-7299.

[9] S.R. Cherkupally and R. Mekalan, Chem. Pharm. Bull., 2008, 56, 1002-1004.

[10] M.M. Heravi, K. Bakhtriri, N.M. Javadi, F.F. Bamoharram, M. Saeedi and H.A. Oskoo, J. Mol. Catal. A Chem., 2007, 264, 50-52.

[11] N.N. Karade, H.V. Budhewar, V.S. Shinde and W.N. Jadhav, Lett. Org. Chem., 2007, 4, 16-19.

[12] C.S. Reddy and M. Raghu, Indian J. Chem., 2008, 47B, 1578-1582.

[13] L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z. Fan, H. Tian and C.T. Qian, Tetrahedron,  2005, 61, 1539-1543.

[14] A. Khazaei, A.R. Moosavi-Zare, H. Afsar – Hezarkhani and V. Khakyzadeh, RSC Adv., 2014, 4, 32142-32147.

[15] G. Song, B. Wang, X. Wu, Y. Kang and L. Yang L, Synth.Commun., 2005, 35, 2875-2880.

[16] J.S. Yoo, T.J. Lauglin, J.J. Krob and R.S. Mohan, Tett. Lett., 2015, 56, 4060-4062.

[17] S.B. Sapkal, K.F. Shelke, B.B. Shingate and M.S. Shingare MS, Tett. Lett., 2009, 50, 1754-1756.

[18] L. Ohberg and J. Westman, Synlett, 2001, 1296-1298.

[19] P. Arumugam and P.T. Perumal, Indian J. Chem. Sec. B, 2008, 47B, 1084-1090.

[20] S. Kumar, P. Sharma, K.K. Kapoor and M.S. Hundal, Tetrahedron, 2008, 64, 536-542.

[21] S.R. Kumar, Y. Venkateswaralu and P. Leelavathi, Organic Synthesis and Medicinal Chemistry, 2012, 1, 11-14. 

[22] A.V. Narsaiah, Lett. Org. Chem., 2007, 4(7), 462-464. 

[23] J.L. Luche and A.L. Gemal, Chem. Commun., 1978, 976-977.

[24] A.V. Narsaiah and K. Nagaiah, Indian J. Chem., Sec. B, 2003, 42B, 2045-2047.

[25] A.V. Narsaiah, J. Orgnomet. Chem., 2007, 692. 3614-3618.

[26] J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tett. Lett., 2000, 41, 9075-9078.

[27] S.S. Pandit, B.D. Vikhe and G.D. Shelke, J. Chem. Sci., 2007, 119, 295-297.