Zwitterionic imidazolium salt of [MOEI]-BSA: An efficient solid acid catalyst-promoted green synthesis of quinoxaline derivatives
محورهای موضوعی : Iranian Journal of CatalysisSami 1 , Maryam Norollahi 2 , Sara Miri 3
1 - Department of Chemistry, Payame Noor University, P.O. BOX 19395-4697 Tehran, Iran.
2 - Department of Chemistry, Payame Noor University, P.O. BOX 19395-4697 Tehran, Iran.
3 - Department of Chemistry, Payame Noor University, P.O. BOX 19395-4697 Tehran, Iran.
کلید واژه: 1, [MOEI]-BSA, quinoxaline synthesis, Solid acid, green chemistry, Heterogeneous catalyst, Diamine, 2-Diketone,
چکیده مقاله :
Easily synthesized1-methyl-3-(2-oxyethyl)-1H-imidazol-3-ium-borate sulfonic acid {[MOEI]-BSA} as a novel catalyst efficiently promoted the synthesis of quinoxaline derivatives via condensation of various diamines with 1,2-dicarbonyl compounds at room temperature conditions in ethanol. This research provides a new method for the synthesis of quinoxalines in good to excellent yields with little catalyst loading. The catalyst could be recycled and reused several times without any loss of efficiency.
[1] B.F. Mirjalili, M.A. Zolfigol,A. Bamoniri, A. Hazar, J. Braz. Chem. Soc., 16 (2005) 877-880.
[2] A.R. Kiasat, F. Kazemi, M.F. Mehrjardi, J. Chin. Chem. Soc., 54 (2007) 1337-1339.
[3] A.R. Kiasat, F. Kazemi, M.F. Mehrjardi, Asian J. Chem., 17 (2005) 2830-2832.
[4] G. Sakata, K. Makino, Y. Kuraswa, Heterocycles, 27 (1988) 2481-2515.
[5] W. He, M.R. Meyers, B. Hanney, A. Spada, G. Blider, H. Galzeinski, D. Amin, S. Needle, K. Page, Z. Jayyosi, H. Perrone, Bioorg. Med. Chem. Lett., 13(2003) 3097-3100.
[6] Y.B. Kim, Y.H. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett., 14 (2004) 541-544.
[7] A. Dell, D.H. William, H.R. Morris, G.A. Smith, J. Feeney, G.C.K. Roberts, J. Am. Chem. Soc., 97 (1975) 2497-2502.
[8] (a) C. Bailly, S. Echepare, F. Gago, M.J. Waring, Anti-Cancer Drug Des., 14 (1999) 291-303; (b) S. Sato, O. Shiratori, K.J. Katagiri, Antibiot., 20 (1967) 270-276.
[9] E.D. Brock, D.M. Lewis, T.I. Yousaf, H.H. Harper, Chem. Abst. WO 9951688, 1999.
[10] K.R. Justin Thomas, V. Marappan, T. L. Jiann, C. Chang-Hao, T. Yuai, Chem. Mater., 17 (2005) 1860-1866.
[11] S. Dailey, J.W. Feast, R.J. Peace, R.C. Saga, S. Till, E.L. Wood, J. Mater. Chem., 11 (2001) 2238-2243.
[12] D.O. Brien, M.S. Weaver, D.G. Lidzey, D.D.C. Bradley, Appl. Phys. Lett., 69 (1996) 881-883.
[13] S. Louis, M.G. Marc, J.W. Jory, P.B. Joseph, J. Org. Chem., 68 (2003) 4179-4188.
[14] E.D. Brock, D.M. Lewis, T.I. Yousaf, H.H. Harper,(The Procter and Gamble Company, USA), WO Patent., 1688, 995 (1999).
[15] M.M. Heravi, K. Bakhtiari, M.H. Tehrani, N.M. Javadi, H.A. Oskooie, ARKIVOC, XVI (2006) 16-22.
[16] S.V. More, M.N.V. Sastry, C.F. Yao, Green Chem., 8 (2006) 91-95.
[17] L. Wang, J. Liu, H. Tian, C. Qian, Synth. Commun., 34 (2004) 1349-1357.
[18] A. Hasaninejad, A. Zare, M.A. Zolfigol, M. Shekouhy, Synth. Commun., 39 (2009) 569-579.
[19] D. Venugopal, M. Subrahmanmyam, Catal. Commun., 2 (2001) 219-223.
[20] H.R. Darabi, S. Mohandessi, K. Aghapoor, F. Mohsenzadeh, Catal. Commun., 8 (2007) 389-392.
[21] A. Hasaninejad, A. Zare, M.R. Mohammadizadeh, Z. Karami, J. Iran. Chem. Soc., 6 (2009) 153-158.
[22] M.M. Heravi, K. Bakhtiari, F.F. Bamoharram, M.H. Tehrani, Monatsh. Chem., 138 (2007) 465-467.
[23] A. Hasaninejad, A. Zare, M.R. Mohammadizadeh, M. Shekouhy, Green Chem. Lett. Rev., 3 (2010) 143-148.
[24] M.M. Heravi, M.H. Tehrani, K. Bakhtiari, H.A. Oskooie, Catal. Commun., 8 (2007) 1341-1344.
[25] C. Srinivas, C.N.S.S.P. Kumar, V.J. Rao, S. Palaniappan, J. Mol. Catal. A: Chem., 265 (2007) 227-230.
[26] S. Sajjadifar, E. Rezaee Nezhad, G. Darvishi, J. Chem., 2013, Article ID 834656, 6 pages (2013).
[27] S. Sajjadifar, H. Saeidian, S. Zare, H. Veisi, S. Rezayati, Iran. Chem. Commun., 1 (2013) 7-24.
[28] S. Sajjadifar, S. Rezayati, Chemical Papers, 68 (2014) 531–539.
[29] S. Sajjadifar, O. Louie, J. Chem., 2013, Article ID 674946, 6 pages (2013).
[30] S. Sajjadifar, E. Rezaee Nezhad, E. Khosravani, Chem. Sci. T., 3 (2014) 292-302.
[31] R.S. Bhosale, S.R. Sarda, S.S. Ardhapure, W.N Jadhav, S.R. Bhusare, R.P. Pawar, Tetrahedron Lett., 46 (2005) 7183-7186.
[32] S.V. More, M.N.V. Sastry, C.C. Wang, C.F. Yao Tetrahedron Lett., 46 (2005) 6345-6348.
[33] W.X. Guo, H.-L. Jin, J.-X. Chen. F. Chen. J.C. Dinga, H.Y. Wu, J. Braz. Chem. Soc., 20 (2009) 1674-1679.
[34] M.M. Heravi, S. Taheri, K. Bakhtiari, H.A. Oskooie, Catal. Commun., 8 (2007) 211-214.
[35] T.K. Huang, L. Shi, R. Wang, X.Z. Guo, X.X. Lu, Chin. Chem. Lett. 20 (2009) 161-164.
[36] G. Mohammadi Ziarani, A. Badiei, M. Haddadpour, Int. J. Chem., 3 (2011) 87-94.
[37] T.K. Huang, R. Wang, L. Shi, X.X. Lu, Catal. Commun., 9 (2008) 1143-1147.
[38] K. Niknam, D. Saberi, M. Mohagheghnejad,Molecules, 14(2009)1915-1926
[39] J.J. Cai, J.P. Zou, X.Q. Pan, W. Zhang, Tetrahedron Lett., 49 (2008) 7386–7390.