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

Iranian Journal of Catalysis

مقاله 17، دوره 5، شماره 2، شهریور 2015، صفحه 175-182   

نوع مقاله: Articles

نویسندگان

Krishnamoorthy Aswin¹؛ Majid Ghashang²؛ Sheik Mansoor^{* 3}

¹Research Department of Chemistry, C. Abdul Hakeem College, Melvisharam – 632 509, India

²Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran

³C. Abdul Hakeem College Bio active Organic Molecule Synthetic Unit, Research Department of Chemistry, Melvisharam - India

چکیده

A new and efficient method has been developed for the synthesis of 4-aryl-7-benzylidene-1,3,4,5,6,7-hexahydro-2H-cyclopenta[d]pyrimidin-2-ones through Biginelli-like reaction of cyclopentanone, with urea/thiourea and aromatic aldehyde employing p-dodecylbenzenesulfonic acid (DBSA) as a recyclable catalyst under solvent-free condition. The recovered catalyst was recycled for further runs. The product formation takes place via a cross-aldol condensation of benzaldehyde with cyclopentanone in the presence of DBSA to produce benzylidene intermediate and subsequent Michael addition. The present approach offers the advantages of short reaction time, mild reaction conditions, high yields and convenient operation. All the products were obtained in good to excellent yields and the structures of the synthesized compounds were established by advanced spectroscopic data.

کلیدواژه‌ها

Biginelli reaction؛ p-Dodecylbenzenesulfonic acid؛ Cyclopenta[d]pyrimidin-2-one؛ One-pot synthesis

مراجع

[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.