D-phenyl alanine-oxalic acid (D-Phe-Ox): A novel nano ionic liquid catalyzing the one-step green synthesis of functionalized spirolactones and dispirodihydro-furanyl oxindoles
الموضوعات : Iranian Journal of CatalysisKobra Nikoofar 1 , Shiva Khani 2
1 - Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, P.O. Box 1993893973, Tehran, Iran.
2 - Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, P.O. Box 1993893973, Tehran, Iran.
الکلمات المفتاحية: Isatin, Chiral, Nano ionic liquid, DMAD, Spirolactone, Dispirodihydrofuranyl oxindole,
ملخص المقالة :
In this paper, a new nano-size ionic liquid (nIL) has been synthesized from D-phenylalanine and oxalic acid (D-Phe-OX) via a simple procedure. The obtained nIL has been characterized by the fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDAX), thermogravimetric analysis (TGA), nuclear magnetic resonance spectroscopy (1H NMR), and field emission scanning electron microscopy (FESEM), techniques. The synthesized nanocatalyst has been used for the three-component one-step synthesis of functionalized spirolactones via the condensation reaction of arylamines, DMAD and isatins. The stereoselective preparation of dispirodihydrofuranyl oxindoles has also been examined successfully through the one-step pseudo-four component condensation of isatins, amines and DMAD, respectively.
[1] a) R. Skoda-Flodes, Molecules 19 (2014) 8840-8884. b) C. Chiappe, D. Pieraccini, J. Phys. Org. Chem. 18 (2005) 275-297. c) T.L. Greaves, C. Drummond, Chem. Rev. 115 (2015) 11379-11448.
[2] A. Dandia, Sh. Khan, P. Soni, A. Indora, D.K. Mahawar, P. Pandy, C.S. Chauhan, Bioorg. Med. Chem. Lett. 27 (2017) 2873-2880.
[3] P. Ramesh, Rao K.S., R. Trivedi, B.S. Kumar, R.S. Prakasham, B. Sridhar, RSC Adv. 6 (2016) 26546-26552.
[4] S.A.S. Ghozlan, M.F. Mohamed, A.G. Ahmed, S.A. Shouman, Y.M. Attia, I.A. Abdelhamid, Arch. Pharm. 348 (2015) 113-124.
[5] G.O. Fonseca, J.M. Cook, Org. Chem. Ins. 6 (2016) 1-55.
[6] J. Sun, H. Gong, Ch. Yan, Chin. J. Chem. 33 (2015) 1049-1056.
[7] G. Rainoldi, F. Begnini, A. Silvani, G. Lesma, Synlett 27 (2016) 2831-2835.
[8] N. Sharma, Zh. Li, U.K. Sharma, E.V. Van der Eycken, Org. Lett. 16 (2014) 3884-3887.
[9] U. Borthakur, M. Borah, M.J. Deka, A.K. Saikia, J. Org. Chem. 81 (2016) 8736-8743.
[10] H.P. Deng, Y. Wei, M. Shi, Org. Lett. 13 (2011) 3348-3351.
[11] a) Gh. Mohammadi Ziarani, R. Moradi, N. Lashgari, Tetrahedron 74 (2018) 1323-1353. b) W.B. Chen, Z.J. Wu, Q.L. Pei, N.F. Cun, X.M. Zhang, W.C. Yuan, Org. Lett. 12 (2010) 3132-3135.
[12] a) L. Hong, R. Wang, Adv. Synth. Catal. 355 (2013) 1023-1052. b) M. Bai, B. Cui, J. Zuo, J. Zhao, Y. You, Y. Chen, X. Xu, X. Zhang, W. Yuan, Tetrahedron 71 (2015) 949-955.
[13] M. Messina, C. Manieri, P. Biffignandi, C. Massucchetti, R.F. Novi, G.M. Molinatti, J. Endocrinol. Invest. 6 (1983) 23-27.
[14] E.M. Peterson, K. Xu, K.D. Holland, A.C. McKeon, S.M. Rothman, J.A. Ferrendelli, D.F. Covey, J. Med. Chem. 37 (1994) 275-280.
[15] T. Hayashi, M. Jean, H. Huang, S. Simpson, N.G. Santoso, J. Zhu, Antivir. Res. 146 (2017) 76-85.
[16] L. Yang, L.H. Qin, S.W. Bligh, A. Bashall, C.F. Zhang, M. Zhang, Z.T. Wang, L.S. Xu, Bioorg. Med. Chem. 15 (2006) 3496-3501.
[17] K. Nikoofar, Z. Khademi, M. Haghighi, J. Chem. Sci. 128 (2016) 1805-1811.
[18] L. Fotouhi, K. Nikoofar, Tetrahedron Lett. 54 (2013) 2903-2905.
[19] K. Nikoofar, Sh. Moazzez Dizgarani, Monatsh. Chem. 146 (2015) 1161-1204.
[20] K. Nikoofar, Z. Khalili, Z.Z. Naturforsch. B Chem. Sci. 71 (2016) 31-36.
[21] K. Nikoofar, S. Gorji, Phosphorus Sulfur Silicon Relat. Elem. 190 (2015) 1138-1145.
[22] K. Nikoofar, M. Haghighi, Z. Khademi, Arab. J. Chem. (2016) doi:10.1016/j.arabjc.2016.01.013.
[23] S.E. Kiruthika, R. Amritha, P.T. Perumal, Tetrahedron Lett. 53 (2012) 3268-3273.
