Brönsted acidic ionic liquid as a recyclable catalyst for the one pot four-component synthesis of substituted pyrano[2,3-c]pyrazoles

Iranian Journal of Catalysis

مقاله 9، دوره 6، شماره 1، خرداد 2016، صفحه 69-74   

نوع مقاله: Articles

نویسندگان

Leila Khazdooz^{* 1}؛ Amin Zarei²

¹Department of Science, Khorasgan Branch, Islamic Azad University, Isfahan 81595-158, Iran.

²Department of Science, Fasa Branch, Islamic Azad University, PO Box No. 364, Fasa 7461713591, Fars, Iran.

چکیده

An efficient, mild and environmentally friendly method was reported for the synthesis of An efficient, mild and environmentally friendly method was reported for the synthesis of pyranopyroles from aryl aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate in the presence of catalytic amounts of Methyl imidazolium hydrogen sulfate ([Hmim][HSO4]) as an efficient catalyst. These syntheses were performed via a one-pot four-component condensation in water/ethanol (50%) at 50 ◦C. This method easily provides the coresponding products in good yield and relatively short reaction times. Also the reusability of the catalyst was investigated, the catalyst could be employed four times, although its activity gradually decreased.

کلیدواژه‌ها

Four-component reaction؛ Pyranopyrazole؛ Aldehydes؛ Hydrazine hydrate؛ Methyl imidazolium hydrogen sulfate

مراجع

[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.