Cellulose sulfuric acid catalyzed multicomponent reaction for efficient synthesis of pyrimido and pyrazolo[4,5-b]quinolines under solvent-free conditions

Document Type: Articles

Author

Young Researchers and Elites Club, Rasht Branch, Islamic Azad University, Rasht, Iran

Abstract

Cellulose sulfuric acid was used as an efficient biopolymer-based catalyst for the synthesis of tetrahydropyrimido[4,5-b]quinoline-2,4,6-triones and hexahydro-2H-pyrazolo[5,4-b]quinoline-6-ones via three component reaction of aldehyde, 5,5-dimethyl-1,3-cyclohexadione and 6-amino-1,3-dimethyluracil or 5-amino-3-methyl-1-phenypyrazole under solvent-free conditions at 90 oC. The major advantages of the present method are simple experimentation, use of inexpensive and eco-friendly reusable catalyst with good yields and short reaction times.

Keywords


[1] B.M. Trost, Science 254 (1991) 1471-1477.

[2] A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39 (2000) 3168-3173.

[3] J. Zhu, H. Bienayme, Multi Component Reactions, Wiley-VCH, Weinheim, 2005.

[4] A. Domling, Chem. Rev. 106 (2006) 17-23.

[5] I. Ugi, Pure Appl. Chem. 73 (2001) 187-191.

[6] R.R. Nagawade, D. B. Shinde, Acta Chim. Slov. 54 (2007) 642-645.

[7] D.M. D'Souza, T.J. Mueller, Chem. Soc. Rev. 36 (2007) 3169-3173.

[8] C.C. A. Cariou, G.J. Clarkson, M. Shipman, J. Org. Chem. 73 (2008) 9762-9764.

[9] C. Kalinski, H. Lemoine, J. Schmidt, C. Burdack, J. Kolb, M. Umkehrer, G. Ross, Synlett (2008) 4007-4011.

[10] R.V.A. Orru, M. De Greef, Synthesis (2003) 1471-1499.

[11] (a) A. Perzyna, F. Klupsch, R. Houssin, N. Pommery, A. Lemoine, J. P. Henichart, Bioorg. Med. Chem. Lett. 14 (2004) 2363-2365. (b) A.A. Joshi, C.L. Viswanathan, Bioorg. Med. Chem. Lett. 16 (2006) 2613-2617. (c) R.M.P. Klingenstein, S.R. Leliveld, A. Ryckebusch, C. Korth, J. Med. Chem. 49 (2006) 5300-5308. (d) A.B.A. El-Gazzar, M.M. Youssef, A.M.S. Youssef, A.A. Abu-Hashem, F.A. Badria, Eur. J. Med. Chem. 44 (2009) 609-624.

[12] G.J. Atwell, B.C. Baguley, W.A. Denny, J. Med. Chem. 32 (1989) 396-401.

[13] (a) S.C. Kuo, H.Z. Lee, J.P. Juang, Y.T. Lin, T.S. Wu, J.J. Chang, D. Lednicer, K.D. Paull, C.M. Lin, E. Hamel, K.H. Lee, J. Med. Chem. 36 (1993) 1146-1156. (b) Y. Xia, Z.Y. Yang, P. Xia, K.F. Bastow, Y. Tachibana, S.C. Kuo, E. Hamel, T. Hackl, K.H. Lee, J. Med. Chem. 41 (1998) 1155-1162.

[14] Y.L. Chen, I. L. Chen, C.C. Tzeng, T.C. Wang, Helv. Chim. Acta 83 (2000) 989-994.

[15] (a) H.I. El-Sabbagh, A.H. Abadi, I.E. Al-Khawad, K.A. Al-Rashood, Arch. Pharm. Pharm. Med. Chem. 332 (1990) 19-24. (b) S.A. Bol, J. Horibeck, J. Markovic, J.G. de Boer, R.J. Turesky, A. Constable, Carcinogenesis 21 (2000) 1-6.

[16] O.A. El-Sayed, M. El-Semary, M.A. Khalid, Alex. J. Pharm. Sci., 10 (1996) 43-46.

[17] T.H. Althuis, P.F. Moore, H.J. Hess, J. Med. Chem. 22 (1979) 44-48.

[18] (a) L.V.G. Nargund, V.V. Badiger, S.M. Yarnal, J. Pharm. Sci. 81 (1992) 365-366. (b) O.A. El-Sayed, F.M.E. El-Baih, Sh.I. El-Aqeel, B.A. Al Bassam, M.E. Hussein, Boll. Chim. Farm. 141 (2002) 461-465.

[19] B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali, N.S. Shetty, Bioorg. Med. Chem. 14 (2006) 2040-2047.

[20] S. Całus, E. Gondek, A. Danel, B. Jarosz, M. Pokładko, A.V. Kityk, Mater. Lett. 61 (2007) 3292-3295.

[21] N.C. Petal, A.G. Mehta, Asian J. Chem. 13 (2001) 1385-1388.

[22] (a) A.K. Agarwal, S.A. Jenekhe, Macromolecules 24 (1991) 6806-6808. (b) X. Zhang, A.S. Shetty, S.A. Jenekhe, Macromolecules 32 (1999) 7422-7429 (c) S.A. Jenekhe, L. Lu, M.M. Alam, Macromolecules 34 (2001) 7315-7324. (d) J.I. Kim, I.S. Shin, H. Kim, J.K. Lee, J. Am. Chem. Soc. 127 (2005) 1614-1615.

[23] (a) A.A. Joshi, C.L. Viswanathan, Anti-lnfec. Agents Med. Chem. 5 (2006) 105-122. (b) A.A. Joshi, S.S. Narkhede, C.L. Viswanathan, Bioorg. Med. Chem. Lett. 15 (2005) 73-76. (c) A. Dlugosz, D. Dus, Farmaco 51 (1996) 364-374. (d) S.T. Selvi, V. Nadaraj, S. Mohan, R. Sasi, M. Hema, Bioorg. Med. Chem. 14 (2006) 3896-3903. (e) O.A. El-Sayed, T.M. Al-Turki, H.M. Al-

Daffiri, B.A. Al-Bassam, M.E. Hussein, Boll. Chim. Farm. 143 (2004) 227-238.

[24] (a) R.G. Stein, J.H. Beil, T. Singh, J. Med. Chem. 13 (1970) 153-155. (b) M. Fujita, H. Egawa, T. Miyamoto, J. Nakano, J. Matsumoto, Eur. J. Med. Chem. 31 (1996) 981-988.

[25] D.Q. Shi, S.N. Ni, F. Yang, J.W. Shi, G.L. Dou, X.Y. Li, X.S. Wang, S.J. Ji, J. Heterocycl. Chem. 45 (2008) 693-702.

[26] G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, Tetrahedron Lett. 53 (2012) 399-402.

[27] M.J. Khurana, A. Chaudhary, B. Nand, A. Lumb, Tetrahedron Lett. 53 (2012) 3018-3022.

[28] F. Nemati, R. Saeedirad, Chin. Chem. Lett. 24 (2013) 370-372.

[29] G.P. Hua, J.N. Xu, S.J. Tu, Q. Wang, J.P. Zhang, X.T. Zhu, T.J. Li, S.L. Zhu, X.J. Zhang, Chin. J. Org. Chem. 25 (2005) 1610-1614.

[30] L.Q. Wu, R.Y. Dong, C.G. Yang, F.L. Yan, J. Chin. Chem. Soc. 57 (2010) 19-23.

[31] C.L. Shi, D.Q. Shi, S.H. Kim, Z.B. Huang, S.J. Ji, M. Ji, Tetrahedron 64 (2008) 2425-2432.

[32] J.V. Madhav, Y.T. Reddy, P.N. Reddy, M.N. Reddy, S. Kumar, P.A. Crooks, B. Rajitha, J. Mol. Catal. A: Chem. 304 (2009) 85-87.

[33] J. Safari, S.H. Banitab, S.D. Khalili, J. Mol. Catal A: Chem. 335 (2011) 46-50.

[34] A. Shaabani, A.H. Rezayan, M. Behnam, M. Heidary, C. R. Chim. 12 (2009) 1249-1252.

[35] A. Shaabani, A. Maleki, Appl. Catal. A: Gen. 331 (2007) 149-151.

[36] A. Shaabani, A. Maleki, J. Moghimi Rad, E. Soleimani, Chem. Pharm. Bull. 55 (2007) 957-958.

[37] A. Shaabani, A. Rahmati, Z. Badri, Catal. Commun. 9 (2008) 13-16.

[38] K.F. Shelke, S.B. Sapkal, G.K. Kakade, B. Bapurao, M.S. Shingare, Green Chem. Lett. Rev. 23 (2010) 27-32.

[39] A. Shaabani, M. Seyyedhamzeh, A. Maleki, F. Rezazadeh, Appl. Catal. A: Gen. 358 (2009) 149-151.

[40] (a) M. Dabiri, S.C. Azimi, H.R. Khavasi, A. Bazgir, Tetrahedron 64 (2008) 7307-7311. (b) M. Dabiri, S.C. Azimi, H.R. Khavasi, A. Bazgir, Monatsh. Chem. 138 (2007) 659-661. (c) K. Rad-Moghadam, S.C. Azimi, Tetrahedron 68 (2012) 9706-9712. (d) K. Rad-Moghadam, S.C. Azimi, E. Abbaspour-Gilandeh, Tetrahedron Lett. 54 (2013) 4633-4636. (e) K. Rad-Moghadam, M. Sharifi-Kiasaraie, S.C. Azimi, Tetrahedron 68 (2012) 6472-6476 (f) K. Rad-Moghadam, S.C. Azimi, J. Mol. Catal. A: Chem. 363 (2012) 465-469.