An efficient synthesis of 4-aryl-7-benzylidene-hexahydro-2H-cyclopenta[d] pyrimidin-2-ones/thiones catalyzed by p-dodecylbenzenesulfonic acid

Subject Areas : Iranian Journal of Catalysis

Krishnamoorthy Aswin ¹ , Majid Ghashang ² , Sheik Mansoor ³

1 - Research Department of Chemistry, C. Abdul Hakeem College, Melvisharam – 632 509, India
2 - Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran
3 - C. Abdul Hakeem College Bio active Organic Molecule Synthetic Unit, Research Department of Chemistry, Melvisharam - India

Received: 2014-12-05 Accepted : 2015-01-15 Published : 2015-06-01

Keywords:

References:

[1] P. Biginelli, Grazz. Chim. Ital. 23 (1893) 360-413.
[2] C.O. Kappe, QSAR Comb. Sci. 22 (2003) 630-645.
[3] C.O. Kappe, Tetrahedron 49 (1993) 6937-6963.
[4] G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. Dimarco, J. Gougoutas, A. Hedberg, M. Malley, J.P. McCarthy, J. Med. Chem. 38 (1995) 119-129.
[5] G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz, M.F. Malley, J. Med. Chem. 35 (1992) 3254–3263.
[6] D. Nagarathnam, S.W. Miao, B. Lagu, M.C. Harrell, K.P. Vyas, C. Gluchowski, J. Med. Chem. 42 (1999) 4764–4777.
[7] J.C. Barrow, P.G. Nantermet, D. Nagarathnam, C. Forray, J. Med. Chem. 43 (2000) 2703–2718.
[8] J. Kim, J. Ok, C. Park, W. So, M. Jo, Y. Kim, Bioorg. Med. Chem. Lett. 22 (2012) 2522-2526.
[9] T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S. L. Schreiber, T.J. Mitchison, Science 286 (1999) 971-974.
[10] A. D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C. De Brosse, S. Mai, A. Truneh, B. Carte, J. Org. Chem. 60 (1995) 1182-1188.
[11] A. Rajack, K. Yuvaraju, Ch. Praveen, Y.L.N. Murthy, J. Mol. Catal. A: Chem. 370 (2013) 197-204.
[12] J.T. Starcevich, T.J. Laughlin, R.S. Mohan, Tetrahedron Lett. 54 (2013) 983-985.
[13] S.R. Jetti, D. Verma, S. Jain, Iran. J. Catal. 3 (2013) 203-209.
[14] J. Albadi, A. Mansournezhad, Iran. J. Catal. 3 (2013) 73-77.
[15] A. Bashti, B. Karami, S. Khodabakhshi, Iran. J. Catal. 4 (2014) 267-272.
[16] D. Shobha, M.A. Chari, A. Mano, S.T. Selvan, K. Mukkanti, A. Vinu, Tetrahedron 65 (2009) 10608-10611.
[17] P. G. Mandhane, R.S. Joshi, D.R. Nagargoje, C.H. Gill, Tetrahedron Lett. 51 (2010) 3138-3140.
[18] Y. Yu, D. Liu, C. Liu, G. Luo, Bioorg. Med. Chem. Lett. 17 (2007) 3508-3510.
[19] M. Wu, J. Yu, W. Zhao, J. Wu, S. Cao, J. Fluorine Chem. 132 (2011) 155-159.
[20] F. Shirini, M.A. Zolfigol, J. Albadi, Chin. Chem. Lett. 22 (2011) 318-321.
[21] Y. Zhu, S. Huang, T. Pan, Euro. J. Org. Chem. 11 (2005) 2354-2367.
[22] H. Zhang, Z. Zhou, Z. Yao, F. Xu, Q. Shen, Tetrahedron Lett. 50 (2009) 1622-1624.
[23] M. Lei, L. Ma, L. Hu, Monatsh. Chem. 141 (2010) 1005-1008.
[24] T.-S. Jin, R.-Q. Zhao, T.-S. Li, ARKIVOC XI (2006) 176-182.
[25] D. Prasad, A. Preetam, M. Nath, C.R. Chim. 15 (2012) 675-678.
[26] T.-S. Jin, J.-S. Zhang, A.-Q. Wang, T.-S. Li, Ultrason. Sonochem. 13 (2006) 220-224.
[27] M.A. Bigdeli, G. Gholami, E. Sheikhhosseini, Chin. Chem. Lett. 22 (2011) 903-906.
[28] Y. Han, Y. Chu, J. Mol. Catal. A: Chem. 237 (2005) 232-237. 
[29] Y.Y. Peng, Q.-L. Zhang, J.-J. Yuan, J.P. Cheng. Chin. J. Chem. 26 (2008) 2228-2232.
[30] H. Hashemi, A. R. Sardarian, Iran. J. Sci. Technol. A1 (2013) 75-82.
[31] E. Sheikhhosseini, D. Ghazanfari, V. Nezamabadi, Iran J. Catal. 3 (2013) 197-201.
[32] E. Sheikhhosseini, S.A. Ahmadi, S. Sadeghi, J. Appl. Chem. Res. 8 (2014) 25-30.
[33] K. Aswin, S.S. Mansoor, K. Logaiya, P. N. Sudhan, R. N. Ahmed, J. Taibah Univ. Sci. 8 (2014)
236–247.
[34] A. Shamsaddini, E. Sheikhhosseini, Int. J. Org. Chem. 4 (2014) 135-141.
[35] M. Ghashang, S.S. Mansoor, K. Aswin, Chin. J. Catal. 35 (2014) 43–48.
[36] M. Ghashang, S.S. Mansoor, K. Aswin, Chin. J. Catal. 35 (2014) 127–133.
[37] M.R.M. Shafiee, S.S. Mansoor, M.Ghashang, A. Fazlinia, C. R. Chim. 17 (2014) 131-134.
[38] M. Ghashang, S.S. Mansoor, K. Aswin, J. Adv. Res. 5 (2014) 209–218.