Green approach for the synthesis of pyranopyrazoles and hexahydroquinoline-3-carboxamides using unripe grape juice (verjuice) as catalyst
محورهای موضوعی : Iranian Journal of Catalysis
1 - Young Researchers and Elite Club, Rasht Branch, Islamic Azad University, Rasht, Iran.
کلید واژه: Multi-component reactions, Pyranopyrazoles, Unripe grape juice, Hexahydroquinoline-3-carboxamides,
چکیده مقاله :
Unripe grape juice (verjuice) as a natural catalyst was successfully applied to perform the one-pot reaction of aryl aldehydes, malononitrile, hydrazine hydrate and ethyl acetoacetate to synthesize pyranopyrazole derivatives in aqueous ethanol at room temperature in excellent yields. Furthermore, unripe grape juice catalyzed one-pot synthesis of hexahydroquinoline-3-carboxamide derivatives by the four-component reaction of arylaldehydes, dimedone, acetoacetanilide and ammonium acetate in high to excellent yield in ethanol at 70 ℃. The synthesized compounds were identified by FT-IR, 1H NMR and 13C NMR spectroscopic techniques and elemental analysis. An environmentally benign procedure, short reaction time, high yields and biocompatible natural catalyst are some advantages of this research.
[1] A.C. Kaliora, A.M. Kountouri, V.T. Karathanos, J. Med. Food 12 (2009)1302-1309.
[2] K.M. Janisch, C. Olschlager, D. Treutter, E.F. Elstner, J. Agric. Food Chem. 54 (2006) 4839-4848.
[3] K. Karthikeyan, B.R. Bai, S.N. Devaraj, J. Cardiovasc. Pharmacol. 53 (2009) 109-115.
[4] W.R. Leifert, M.Y. Abeywardena, Nutr. Res. 28 (2008) 842-850.
[5] M.S.P. Nikfardjam, Mitt. Klosterneuburg 58 (2008) 28-31.
[6] M. Karapinar, I.Y. Sengun, Food Control. 18 (2007) 702-706.
[7] I. Hayoglu, O. Kola, C. Kaya, S. Özer, H. Turkoglu, J. Food Process Preserv. 33 (2009) 252-263.
[8] S. Karabiyikli, N. Öncül, J. Food Process Preserv. 40 (2016) 459–1465.
[9] A.D. de Matos, A. Curioni, A.T. Bakalinsky, M. Marangon, G. Pasini, S. Vincenzi, Innov. Food Sci. Emerg. Technol. 44 (2017) 9-14.
[10] M. Setorki, B. Nazari, S. Asgary, L. Azadbakht, M. Rafieian-Kopaei, Afr. J. Pharm. Pharacol. 5(2011) 1038-1045.
[11] M. Alipour, P. Davoudi, Z. Davoudi, J. Med. Plants Res. 6 (2012) 5677-5683.
[12] B. Zolfaghari, M. Kazemi, M. Nematbakhsh, Adv. Biomed. Res. 4 (2015) 109-112.
[13] S. Soares, R. Vitorino, H. Osório, A. Fernandes, A. Venâncio, N. Mateus, F. Amado, V. de Freitas, J. Agric. Food Chem. 59 (2011) 5535-5547.
[14] H. Adibi, L. Hosseinzadeh, S. Farhadi, F. Ahmadi, J. Reports Pharma Sci. 2 (2013) 116-124.
[15] M.E.A. Zaki, H.A. Saliman, O.A. Hiekal, A.E.Z. Rashad, Naturforsch. C: Biosci. 61 (2006) 1-5.
[16] N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14 (2006) 4792-4802.
[17] F.M. Abdelrazek, P. Metz, N.H. Metwally, S.F. El-Mahrouky, Arch. Pharm. 339 (2006) 456-460.
[18] A.R. Moosavi-Zare, M.A. Zolfigol, E. Noroozizadeh, M. Tavasoli, V. Khakyzadeh, A. Zare, New J. Chem. 37 (2013) 4089-4094.
[19] H. Kiyani, H.A. Samimi, F. Ghorbani, S. Esmaieli, Curr. Chem. Lett. 2 (2013) 197-206.
[20] G. Brahmachari, B. Banerjee, ACS Sust. Chem. Eng. 2 (2014) 411-422.
[21] C.F. Zhou, J.J. Li, W.K. Su, Chin. Chem. Lett. 27 (2016)1686–1690.
[22] E. Soleimani, M. Jafarzadeh, P. Norouzi, J. Dayou, C.S. Sipaut, R.F. Mansa, P. Saei, J. Chin. Chem. Soc. 62 (2015)1155-1162.
[23] H. Mecadon, M.R. Rohman, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 2523-2525.
[24] H. Mecadon, M.R. Rohman, I. Kharbangar, B. M. Laloo, I. Kharkongor, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 3228–3231.
[25] Y.A. Tayade, S.A. Padvi, Y.B. Wagh, D.S. Dalal, Tetrahedron Lett. 56 (2015) 2441-2447.
[26] M. Wu, Q. Feng, H.D. Wan, J. Ma, Synth. Commun. 43 (2013) 1721-1726.
[27] A.B. Atar, J.T. Kim, K.T. Lim, Y.T. Jeong, Synth. Commun. 44 (2014) 2679-2691.
[28] R.H. Vekariya, K.D. Patel, H. Patel, Res. Chem. Intermed. 42 (2016) 4683–4696.
[29] J.M. Khurana, A. Chaudhary, Green Chem. Lett. Rev. 5 (2012) 633-638.
[30] S.U. Tekale, S.S. Kauthale, K.M. Jadhav, R.P. Pawar, J. Chem. (2013) ID 840954.
[31] R.H. Vekariya, K.D. Patel, H. Patel, Res. Chem. Intermed. 42 (2016) 7559-7579.
[32] B. Sushilkumar, S. Devanand, Acta Pharm. 52 (2002) 281-287.
[33] R. Boer, V. Gekeler, Drugs Future 20 (1995) 499-509.
[34] G.A. Wachter, M.C. Davis, J. Med. Chem. 41(1998) 2436-2438.
[35] S. Gullapalli, P. Ramarao, Neuropharmacology 42 (2002) 467-475.
[36] C.E. Sunkel, M. de Casa Juana, L. Santos, J. Med. Chem. 33 (1990) 3205-3210.
[37] V. Klusa, Drugs Future 20 (1995) 135-138.
[38] R.G. Retzel, C.C. Bollen, E. Maeser, K.F. Federlin, Drugs Future 17 (1992) 465-468.
[39] K. Ahmed, A.K. Jain, B. Dubey, B. Shrivastava, P. Sharma, S. Nadeem, Der Pharma Chem. 7 (2015) 52-65.
[40] V.L. Gein, M.I. Kazantseva, A.A. Kurbatova, M.I. Vahrin, Chem. Heterocycl. Compd. 46 (2010) 629-630.
