Highly efficient synthesis of carboacyclic nucleosides catalyzed by zinc oxide in 1-butyl-3-methylimidazolium bromide (ZnO/[bmim]Br)

محورهای موضوعی : Iranian Journal of Catalysis

Tarlan Salehi-Hamzehkhani ¹ , Marzieh Hatami ² , Abdolkarim Zare ³ , Ahmad Reza Moosavi-Zare ⁴ , Abolfath Parhami ⁵ , Zahra Khedri ⁶ , Hamideh Kabgani ⁷ , Mohammad Beikagha ⁸ , Raheleh Salamipoor ⁹

1 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
2 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
3 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
4 - Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad, 6541835583, Iran.
5 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
6 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
7 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
8 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
9 - Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.

تاریخ دریافت : 1393/01/17 تاریخ پذیرش : 1393/03/12 تاریخ انتشار : 1393/09/10

کلید واژه: Ionic Liquid, Zinc oxide, Microwave irradiation, Carboacyclic nucleoside, Michael addition, 1-Butyl-3-methylimidazolium bromide ([bmim]Br),

چکیده مقاله :

Michael addition of pyrimidine and purine nucleobases to substituted as well as unsubstituted α,β-unsaturated esters efficiently proceeds in the presence of catalytic amount of zinc oxide in ionic liquid 1-butyl-3-methylimidazolium bromide (ZnO/[bmim]Br) under microwave irradiation to afford carboacyclic nucleosides, as biologically important compounds, in good to excellent yields and in short reaction times.

منابع و مأخذ:

[1] K. Mikami, Green Reaction Media in Organic Synthesis, Blackwell Publishing, Oxford, UK (2005).
[2] R. D. Rogers, Ionic Liquids as Green Solvents: Progress and Prospects, ACS Symposium Series 856, American Chemical Society, Washington DC (2003).
[3] P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim (2003).
[4] A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri Rad, J. Comb. Chem. 12 (2010) 844-849.
[5] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A: Gen. 467 (2013) 61-68.
[6] A. Zare, F. Abi, A.R. Moosavi-Zare, M.H. Beyzavi, M.A. Zolfigol, J. Mol. Liq. 178 (2013) 113-121.
[7] A.R. Moosavi-Zare, M.A. Zolfigol, E. Noroozizadeh, M. Tavasoli, V. Khakyzadeh, A. Zare, New J. Chem. 37 (2013) 4089-4094.
[8] A. Zare, R. Khanivar, M. Merajoddin, M. Kazem-Rostami, M.M. Ahmad-Zadeh, A.R. Moosavi-Zare, A. Hasaninejad, Iran. J. Catal. 2 (2012) 107-114.
[9] E. Rezaee Nezhad, S. Sajjadifara, S. Miria, S. Karimiana, Z. Abbasi, Iran. J. Catal. 3 (2013) 191-196.
[10] L. Roux, S. Priet, N. Payrot, C. Weck, M. Fournier, F. Zoulim, J. Balzarini, B. Canard, K. Alvarez, Eur. J. Med. Chem. 63 (2013) 869-881.
[11] T. Tichy, G. Andrei, R. Snoeck, J. Balzarini, M. Dracínsky, M. Krecmerova, Eur. J. Med. Chem. 55 (2012) 307-314.
[12] G. Thomas, An Introduction to Medicinal Chemistry, John Wiely & Sons Inc., Chichester (2000).
[13] E.C. Taylor, F. Sowinski, J. Am. Chem. Soc. 91 (1969) 2143-2144.
[14] J.L. Kelley, R.M. Bullock, M.P. Krochmal, E.W. McLean, J.A. Linn, M.J. Durcan, B.R. Cooper, J. Med. Chem. 40 (1997) 3207-3216.
[15] F.C. Tucci, Y.-F. Zhu, Z. Guo, T.D. Gross, P.J. Connors, Y. Gao, M.W. Rowbottom, R.S. Struthers, G.J. Reinhart, Q. Xie, T.K. Chen, H. Bozigian, A.L. K. Bonneville, A. Fisher, L. Jin, J. Saunders, C. Chen, J. Med. Chem. 47 (2004) 3483-3492.
[16] P. Jansa, O. Baszczynski, M. Dracinsky, I. Votruba, Z. Zidek, G. Bahador, G. Stepan, T. Cihlar, R. Mackman, A. Holy, Z. Janeba, Eur. J. Med. Chem. 46 (2011) 3748-3754.
[17] T. Gazivoda, S. Raic-Malic, V. Kristafor, D. Makuc, J. Plavec, S. Bratulic, S. Kraljevic-Pavelic, K. Pavelic, L. Naesens, G. Andrei, R. Snoeck, J. Balzarini, M. Mintas, Bioorg. Med. Chem. 16 (2008) 5624-5631.
[18] C. Gimbert, M. Moreno-Manas, E. Perez, A. Vallribera, Tetrahedron 63 (2007) 8305-8310.
[19] A. Zare, A. Hasaninejad, R. Safinejad, A.R. Moosavi-Zare, A. Khalafi-Nezhad, M.H. Beyzavi, M. Miralai-Moredi, E. Dehghani, P. Kazerooni-Mojarrad, Arkivoc 16 (2008) 51-64.
[20] H.B. Lazrek, A. Rochdi, H. Khaider, J.L. Barascut, J.L. Imbach, J. Balzarini, M. Witvrouw, C. Pannecouque, E. De Clercq, Tetrahedron 54 (1998) 3807-3816.
[21] H.B. Lazrek, H. Khaider, A. Rochdi, J.L. Barascut, J.L. Imbach, Tetrahedron Lett. 37 (1996) 4701-4704.
[22] A. Khalafi-Nezhad, A. Zare, M.N. Soltani Rad, B. Mokhtari, A. Parhami, Synthesis (2005) 419-424.
[24] Y. Cai, X.-F. Sun, N. Wang, X.F. Lin, Synthesis (2004) 671-674.
[24] S. Boncel, M. Mączka, K.Z. Walczak, Tetrahedron 66 (2010) 8450-8457.
[25] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, A.R. Hasaninejad, Iran. J. Chem. Chem. Eng. 29 (2010) 67-73.
[26] A. Zare, A. Hasaninejad, M.H. Beyzavi, A. Parhami, A.R. Moosavi Zare, A. Khalafi-Nezhad, Can. J. Chem. 86 (2008) 317-324.
[27] M.H. Sarvari, H. Sharghi, J. Org. Chem. 69 (2004) 6953-6956.
[28] M.H. Sarvari, Synthesis (2005) 787-790.
[29] B. Sadeghi, F. Karimi, Iran. J. Catal. 3 (2013) 1-7.
[30] Z.N. Siddiqui, N. Ahmed, F. Farooq, K. Khan, Tetrahedron Lett. 54 (2013) 3599-3602.
[31] F. Tamaddon, M.A. Amrollahi, L. Sharafat, Tetrahedron Lett. 46 (2005) 7841-7844.
[32] A. Loupy, Microwaves in organic synthesis, Wiley-VCH, Weinheim (2006).
[33] M.S. Singh, S. Chowdhury, RSC Adv. 2 (2012) 4547-4592.
[34] A. Zarei, Iran. J. Catal. 2 (2012) 7-16.
[35] A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri-Rad, Green Chem. 13 (2011) 958-964.
[36] A. Zare, A. Hasaninejad, A.R. Moosavi-Zare, M.H. Beyzavi, A. Khalafi-Nezhad, N. Pishahang, Z. Parsaee, P. Mahdavinasab, N. Hayati, Arkivoc 16 (2008) 178-188.
[37] M.N. Soltani Rad, A. Khalafi-Nezhad, S. Behrouz, M.A. Faghihi, A. Zare, A. Parhami, Tetrahedron 64 (2008) 1778-1785.
[38] A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Soltani Rad, G.R. Nejabat, Synth. Commun. 36 (2006) 3549-3562.
[39] A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Soltani Rad, Arkivoc 12 (2006) 161-172.
[40] J.M. Xu, C. Qian, B.K. Liu, Q. Wu, X.F. Lin, Tetrahedron 63 (2007) 986-990.
[41] J.L. Wang, J.M. Xu, Q. Wu, D.S. Lv, X.F. Lin, Tetrahedron 65 (2009) 2531-2536.