One-pot synthesis of tetrahydropyrimido[4,5-b]quinoline derivatives using sulfonic acid functionalized SBA-15 and their antimicrobial activities
الموضوعات : Iranian Journal of CatalysisGhodsi Mohammadi Ziarani 1 , Narges Hosseini Nasab 2 , Mahshid Rahimifard 3 , Taraneh Hajiashrafi 4 , Alireza Badiei 5 , Ali Abolhassani Soorki 6
1 - Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran.
2 - Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran.
3 - Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran.
4 - Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran.
5 - School of Chemistry, College of Science, University of Tehran, Tehran, Iran.
6 - ACECR-Research Institute of Applied Sciences, Shahid Beheshti University, Tehran, Iran.
الکلمات المفتاحية: Aldehydes, Dimedone, Multi-component reaction, 4(6)-Amino uracil, SBA-15-Pr-SO3H,
ملخص المقالة :
A Simple and efficient method for synthesis of tetrahydropyrimido[4,5-b]quinoline derivatives via three component reaction of aromatic aldehydes, dimedone and 6-amino uracil derivatives using a catalytic amount of sulfonic acid functionalized nanoporous silica (SBA-15-Pr-SO3H) is described. The advantages of this method are easy and clean work-up, high yield, mild reaction condition, reusable catalyst and environmentally benign solvents. Antibacterial and antifungal activities of synthesized compounds were measured against gram positive, gram negative bacteriaand fungus. Only compounds 4c and 4g showed activity against Staphylococcus aureus.
[1] J. Zhu, Eur. J. Chem. 2003 (2003) 1133-1144.
[2] V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, L. Balagopal, Accounts Chem. Res. 36 (2003) 899-907.
[3] B.M. Trost, Accounts Chem. Res. 35 (2002) 695-705.
[4] P.A. Wender, V.A. Verma, T.J. Paxton, T.H. Pillow, Accounts Chem. Res. 41 (2008) 40-49.
[5] P.J. Bhuyan, H.N. Borah, J.S. Sandhu, J. Chem. Soc. Perkin Trans. 1 (1999) 3083-3084.
[6] R. Pontikis, C. Monneret, Tetrahedron Lett. 35 (1994) 4351-4354.
[7] A.N. Geisman, V.T. Valuev-Elliston, A.A. Ozerov, A.L. Khandazhinskaya, A.O. Chizhov, S.N. Kochetkov, C. Pannecouque, L. Naesens, K.L. Seley-Radtke, M.S. Novikov, Bioorg. Med. Chem. 24 (2016) 2476-2485.
[8] Maolake, K. Izumi, R. Takahashi, S. Itai, K. Machioka, H. Yaegashi, T. Nohara, Y. Kitagawa, Y. Kadono, H. Konaka, A. Mizokami, M. Namiki, Anticancer Res. 35 (2015) 1603-1606.
[9] S. Perrone, M. Capua, A. Salomone, L. Troisi, J. Org. Chem. 80 (2015) 8189-8197.
[10] S. Majumder, P. Borah, P.J. Bhuyan, Tetrahedron Lett. 55 (2014) 1168-1170.
[11] S. Ahadi, A. Bazgir, J. Iran. Chem. Soc. (2016) 1-7.
[12] D.-Q. Shi, L.-H. Niu, H. Yao, H. Jiang, J. Heterocycl. Chem. 46 (2009) 237-242.
[13] P.K. Basu, A. Ghosh, J. Iran. Chem. Soc. 10 (2013) 55-62.
[14] S. Youssif, S. EI-Bahaie, E. Nabih, Bull. Korean Chem. Soc. 24 (2003) 1429-1432.
[15] M.S. Behalo, G. Mele, J. Heterocycl. Chem. (2016).
[16] D. Heber, C.U. Heers Ravens, Pharmazie 48 (1993) 537-541.
[17] S.P. Satasia, P.N. Kalaria, D.K. Raval, Org. Biomol. Chem. 12 (2014) 1751-1758.
[18] K.M. Abu-Zied, T.K. Mohamed, O.K. Al-Duiaj, M.E. Zaki, Heterocycl. Commun. 20 (2014) 93-102.
[19] J. Quiroga, P.E. Romo, A. Ortiz, J.H. Isaza, B. Insuasty, R. Abonia, M. Nogueras, J. Cobo, J. Mol. Struct. 1120 (2016) 294-301.
[20] K. Bahrami, M.M. Khodaei, P. Fattahpour, Catal. Sci. Technol. 1 (2011) 389-393.
[21] R. van Grieken, J.A. Melero, G. Morales, J. Mol. Catal. A: Chem. 256 (2006) 29-36.
[22] D. Margolese, J.A. Melero, S.C. Christiansen, B.F. Chmelka, G.D. Stucky, Chem. Mater. 12 (2000) 2448-2459.
[23] S. Rostamizadeh, L. Tahershamsi, N. Zekri, J. Iran. Chem. Soc. 12 (2015) 1381-1389.
[24] G. Mohammadi Ziarani, N. Lashgari, A.R. Badiei, Sci. Iran. 20 (2013) 580-586.
[25] G. Mohammadi Ziarani, N. Hosseini Nasab, M. Rahimifard, A. Abolhasani Soorki, J. Saudi Chem. Soc. 19 (2015) 676-681.
[26] G. Mohammadi Ziarani, M. Rahimifard, F. Nouri, A. Badiei, J. Serb. Chem. Soc. 80 (2015) 1265-1272.
[27] G. Mohammadi Ziarani, P. Hajiabbasi, A. Badiei, J. Iran. Chem. Soc. 12 (2015) 1649-1654.
[28] G. Mohammadi Ziarani, S. Faramarzi, N. Lashgari, A. Badiei, J. Iran. Chem. Soc. 11 (2014) 701-709.
[29] V. Fathi Vavsari, G. Mohammadi Ziarani, A. Badiei, S. Balalaie, J. Iran. Chem. Soc. 13 (2016) 1037-1043.
[30] G. Mohammadi Ziarani, M. Rahimifard, A. Badiei, A. Abolhasani Soorki, Iranian Journal of Catalysis 6 (2016) 369-375.
[31] G. Mohammadi Ziarani, A. Badiei, M. Haddadpour, Int. J. Chem. 3 (2011) 87-94.
[32] G. Mohammadi Ziarani, A.R. Badiei, Y. Khaniania, M. Haddadpour, Iran. J. Chem. Chem. Eng. 29 (2010) 1-10.
[33] G. Mohammadi Ziarani, A. Abbasi, A. Badiei, Z. Aslani, E-J. Chem. 8 (2011) 293-299.
[34] M.H. Mosslemin, M.R. Nateghi, Ultrason. Sonochem. 17 (2010) 162-167.
[35] D.-Q. Shi, L.-H. Niu, H. Yao, H. Jiang, J. Heterocycl. Chem. 46 (2009) 237-242.
[36] 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.
[37] G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, Tetrahedron Lett. 53 (2012) 399-402.
[38] NCCLS, in Approved Standard M7-A5. (Villanova, 2000).