Brönsted acidic ionic liquid as a recyclable catalyst for the one pot four-component synthesis of substituted pyrano[2,3-c]pyrazoles
Subject Areas : Iranian Journal of CatalysisLeila Khazdooz 1 , Amin Zarei 2
1 - Department of Science, Khorasgan Branch, Islamic Azad University, Isfahan 81595-158, Iran.
2 - Department of Science, Fasa Branch, Islamic Azad University, PO Box No. 364, Fasa 7461713591, Fars, Iran.
Keywords:
Abstract :
[1] (a) P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice; Oxford University Press: Oxford, UK, 1998. (b) P.T. Anastas, T. Williamson, Green Chemistry, Frontiers in Benign Chemical Synthesis and Process; Oxford University Press: Oxford, UK, 1998.
[2] J. Zhu, H. Bienayme (Eds.), Multicomponent Reactions in the Total Synthesis of Natural Products, Wiley-VCH, Weinheim, 2005.
[3] E. McDonald, K. Jones, P.A. Brough, M.J. Drysdale,
P. Workman, Curr. Top. Med. Chem. 6 (2006) 1193-1203.
[4] N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72 (2007) 3443-3453.
[5] J. Elguero, P. Goya, N. Jagerovic, A.M.S. Silva, Targets Heterocycl. Syst. 6 (2002) 52-98.
[6] (a) J. Zhu, H. Bienayme, In Multicomponent Reactions; J. Zhu, H. Bienayme, Eds. WILEY-VCH Verlag GmbH & Co: KGaA, Weinheim, 2005. (b) D. Tejedor, F. Garcia-Tellado, Chem. Soc. Rev. 36 (2007) 484491. (c) I. Ugi, Pure Appl. Chem. 73 (2001) 187-191. (d) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. (2004) 4957-4980. (e) L. Weber, Drug Discovery Today 7 (2002) 143-147.
[7] I. Hermecz, L. Vasvari-Debreczy, P. Matyus, In Comprehensive Heterocyclic Chemistry; A.R. Katritzky, C.W. Rees, E.V.F. Scriven, Eds.; Pergamon: London, (1996) 563-595.
[8] (a) M. Jayaraman, B.M. Fox, M. Hollingshead,
G. Kohlhagen, Y. Pommier, M. Cushman, J. Med. Chem. 45 (2002) 242-249. (b) R.J. Griffin, G. Fontana, B.T. Golding, S. Guiard, I.R. Hardcastle, J.J.J. Leahy,
N. Martin, C. Richardson, L. Rigoreau, M. Stockley, G.C.M. Smith, J. Med. Chem. 48 (2005) 569-585.
(c) M. Goldbrunner, G. Loidl, T. Polossek, A. Mannschreck, E. von Angerer, J. Med. Chem. 40 (1997) 3524-3533.
[9] D. Ruppert, K.U. Weithmann, Life Sci. 31 (1982) 2037-2043.
[10] J.F. Swinbourne, H.J. Hunt, G. Klinkert, Adv. Heterocycl. Chem. 23 (1987) 103-170.
[11] K. Kuppusamy, P. Kasi, Tetrahedron Lett. 51 (2010) 3312-3316.
[12] E.S. El-Tamany, F.A. El-Shahed, B.H. Mohamed, J. Serb. Chem. Soc. 64 (1999) 9-18.
[13] Z.H. Ismail, G.M. Aly, M.S. El-Degwi, H.I. Heiba, M.M. Ghorab, Egypt J. Biot. 13 (2003) 73-82.
[14] M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, A.E.Z. Rashad, Naturforsch C 61 (2006) 1-5.
[15] F.M. Abdelrazek, P. Metz, N.H. Metwally, S.F. El-Mahrouky, Arch. Pharm. 339 (2006) 456-460.
[16] F.M. Abdelrazek, P. Metz, O. Kataeva, A. Jaeger, S.F. El-Mahrouky, Arch. Pharm. 340 (2007) 543-548.
[17] (a) N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S.; Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14 (2006) 4792-4802. (b) A. Kimata, H. Nakagawa, R. Ohyama, T. Fukuuchi, S. Ohta, T. Suzuki, N. Miyata, J. Med. Chem. 50 (2007) 5053-5056.
[18] (a) V.Y. Sosnovskikh, M.A. Barabanov, B.I. Usachev, R.A. Irgashev, V.S. Moshkin, Russ. Chem. Bull. Int. Ed. 54 (2005) 2846-2850. (b) S.A. El-Assiery, G.H. Sayed, A. Fouda, Acta Pharm. 54 (2004) 143-150.
[19] (a) H. Wamhoff, E. Kroth, K. Strauch, Synthesis (1993) 1129-1132. (b) G.Tacconi, G. Gatti, G. Desimoni, V. Messori, J. Prakt. Chem. 322 (1980) 831-834.
[20] L.A. Rodinovskaya, A.V. Gromova, A.M. Shestopalov, V.N. Nesterov, Russ. Chem. Bull. Int. Ed. 52 (2003) 2207-2213.
[21] H. Junek, H. Aigner, Chem. Ber. 106 (1973) 914-921.
[22] Y.A. Sharanin, L.G. Sharanina, V.V. Puzanova, Zh. Org. Khim. 19 (1983) 2609–2615.
[23] (a) A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova, D.H. Evans, Tetrahedron 59 (2003) 7491-7496. (b) A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova, D.H. Evans, Org. Lett. 4 (2002) 423-425.
[24] Y. Peng, G. Song, R. Ruiling Dou, Green Chem. 8 (2006) 573-575.
[25] G. Vasuki, K. Kandhasamy, Tetrahedron Lett. 49 (2008) 5636–5638.
[26] A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova, D.H. Evans, Tetrahedron 59 (2003) 7491–7496.
[27] A. Siddekhab, A. Nizama, M.A. Pashaa, Spectrochim. Acta, Part A 81 (2011) 431– 440.
[28] P.P. Bora, M. Bihani, G. Bez, J. Mol. Catal. B: Enzym. 92 (2013) 24–33.
[29] G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49 (2008) 5636–5638.
[30] S. Hamood, S. Azzam, M. A. Pasha, Tetrahedron Lett. 53 (2012) 6834–6837.
[31] K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 51 (2010) 3312–3316.
[32] L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhan, Iran. J. Catal. 4 (2012) 173-178.
[33] L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhan, Iran. J. Catal. 11 (2011) 1-9.
[34] A. Zarei, L. Khazdooz, A.R. Hajipour, Dyes Pigm. 85 (2010) 133-138.
[35] A.R. Hajipour, L. Khazdooz, A. Zarei, Synth. Commun. 41 (2011) 2200–2208.
[36] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Catal. Commun. 9 (2008) 89-96.
[37] H. Mecadon, M.R. Rohman, I. Kharbangar, B.M. Laloo, I. Kharkongor, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 3228–3231.
[38] H. Mecadon, M.R. Rohman, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 2523-2525.
[39] A.B. Atar, J.T. Kim, K.T. Lim, Y. T. Jeong, Synth. Commun. 44 (2014) 2679-2691.
[40] F. Tamaddon, M. Alizadeh, Tetrahedron Lett. 55 (2014) 3588–3591.
[41] P.P. Bora, M. Bihani, G. Bez, J. Mol. Catal. B: Enzym. 92 (2013) 24-33.
[42] Y. Zou, H. Wu, Y. Hu, H. Liu , X. Zhao, H. Ji, D. Shi, Ultrason. Sonochem. 18 (2011) 708–712.
