L-Proline catalyzed synthesis of Betti bases and biscoumarin derivatives

Document Type: Articles

Authors

Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran

Abstract

The direct three component modified Mannich reaction via condensation of aldehydes, 2-naphthol or 2,7-naphthalendiol and piperidine to generate Betti bases has been carried out over L-proline (20 mol%) with high efficiency under solvent free conditions at 70 OC. Also, the reaction of aromatic aldehyde and 4-hydroxycoumarin in the presence of L-proline (20 mol%) in the ethanol under reflux conditions, lead to biscoumarin derivatives

Keywords


[1] T.H. Al-Tel, R.A. Al-Qawasmeh, W. Voelter, Eur. J. Org. Chem. (2010) 5586-5593.
[2] A. Basso, L. Banfi, R. Riva, Eur. J. Org. Chem. (2010) 1831-1841.
[3] N. Ma, B. Jiang, G. Zhang, S.J. Tu, W. Wever, G. Li, Green. Chem. 12 (2010) 1357-1361.
[4] C. Haurena, E.L. Gall, S. Sengmany, T. Martens, M. Troupel, J. Org. Chem. 75 (2010) 2645-2650.
[5] M. Adib, E. Sheikhi, A. Kavoosi, H.R. Bijanzadeh, Tetrahedron 66 (2010) 9263-9269.
[6] W.B. Chen, Z.J. Wu, Q.L. Pei, L.F. Cun, X.M. Zhang, W.C. Yuan, Org. Lett. 12 (2010) 3132-3135.
[7] M.S. Singh, S. Chowdhury, RSC Adv. 2 (2012) 4547-4592.
[8] B. Zhang, L. Cai, H. Song, Z. Wang, Z. He, Adv. Synth. Catal. 352 (2010) 97-102.
[9] P.T. Anastas, T.C. Wiliamson, Designing chemistry for the environments, American Chemical Society, Washington DC, 1996.
[10] M. Eissen, J.O. Metzger, E. Schmidt, U. Scheneidwind, Angew. Chem. 114 (2002) 402-425.
[11] G. Guillena, D.J. Ramon, M. Yus, Tetrahedron Asymmetry 18 (2007) 693-700.
[12] M. Betti, Gazz. Chim. Ital. 31 (1900) 301.
[13] M. Betti, Org. Synth. Collect. 1 (1941) 381-383.
[14] C. Cardellicchio, M.A.M. Capozzi, F. Naso, Tetrahedron Asymmetry 21 (2010) 507-517.
[15] A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34 (1999) 877-882.
[16] A. Kumar, M.K. Gupta, M. Kumar, Tetrahedron Lett. 51 (2010) 1582-1582.
[17] A. Jha, N. Paul, K.S. Trikha, T.S. Cameron, Can. J. Chem. 84 (2006) 843-853.
[18] B. Karmakar, J. Banerji, Tetrahedron Lett. 52 (2011) 4957-4960.
[19] S.D. Dindulkar, V.G. Puranik, Y.T. Jeong, Tetrahedron Lett. 53 (2012) 4376-4380.
[20] N. Hamdi, M.C. Puerta, P. Valerga, Eur. J. Med. Chem. 43 (2008) 2541-2548.
[21] Kh.M. Khan, S. Iqbal, M.A. Lodhi, Gh.M. Maharvi, Z. Ullah, M.I. Choudhary, A. Rahman, Sh. Perveen, Bioorg. Med. Chem. 12 (2004) 1963–1968.
[22] M. Kidwi, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 268 (2007) 76-81.
[23] S. Qadir, A. Ahmad Dar, Kh. Zaman Khan, Synth. Commun. 38 (2008) 3490-3499.
[24] N. Hamdi, M.C. Puerta, P. Valerga, Eur. J. Med. Chem. 43 (2008) 2541-2548.
[25] J.M. Khurana, S. Kumar, Tetrahedron Lett. 50 (2009) 4125-4127.
[26] H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7 (2010) 890-894.
[27] N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharram, A. Davoodnia, M. Ghassemzadeh, J. Mol. Liq. 163 (2011) 122-127.
[28] Z. Zareai, M. Khoobi, A. Ramazani, A. Foroumadi, A. Souldozi, K. Slepokura, T. Lis, A. Shafiee, Tetrahedron 68 (2012) 6721-6726.
[29] D. Prasad, A. Preetam, M. Nath, C. R. Chim. 16 (2013) 1153-1157.
[30] A. Nasreen, Tetrahedron Lett. 54 (2013)
3797-3800.
[31] H. Mecadon, M.R. Rohman, I. Kharbangar, B.M. Laloo, I. Kharkongor, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 3228-3