Multicomponent preparation of highly functionalized piperidines using FeCl3.6H2O as an efficient catalyst
محورهای موضوعی : Iranian Journal of CatalysisJasem Aboonajmi 1 , Malek Taher Maghsoodlou 2 , Nourallah Hazeri 3 , Mojtaba Lashkari 4 , Mohyeddin Safarzaei 5 , Moheb Shirzaei 6
1 - Department of Chemistry, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran.
2 - Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran.
3 - Department of Chemistry, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran.
4 - Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran
5 - Department of Chemistry, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran.
6 - Department of Chemistry, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran.
کلید واژه: Aldehyde, Multicomponent, Functionalized piperidine, β-Keto ester,
چکیده مقاله :
FeCl3.6H2O was used as an efficient catalyst for the synthesis of highly functionalized piperidines via a one-pot five-component reaction of aromatic amines, aromatic aldehydes and β-keto esters in EtOH at room temperature. The remarkable advantages offered by this method are good yields, simple procedure, short reaction times, no need to column chromatography and easy work-up. The structures of all compounds were characterized by comparison of their IR and NMR spectra with authentic samples. Also, the relative stereochemistry of these piperidines has been confirmed by single X-ray crystallography analysis in previously reported literature. Starting materials with electron-deficient or electron-releasing groups were reacted efficiently.
[1] A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39 (2000) 3168-3210.
[2] A. Dömling, Chem. Rev. 106 (2006) 17-89.
[3] L.F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. 32 (1993) 131-163.
[4] L.F. Tietze, Chem. Rev. 96 (1996) 115-136.
[5] S.L. Schreiber, Science, 287 (2000) 1964.
[6] M.D. Burke, S.L. Schreiber, Angew. Chem. Int. Ed. 43 (2004) 46-58.
[7] L.F. Tietze, A. Modi, Med. Res. Rev. 20 (2000) 304-322.
[8] C. Grondal, M. Jeanty, D. Enders, Nature. Chem. 2 (2010) 167-178.
[9] K.C. Nicolaou, J.S. Chen, Chem. Soc. Rev. 38 (2009) 2993-3009.
[10] B.B. Tour, D.G. Hall, Chem. Rev. 109 (2009) 4439-4486.
[11] M. Colombo, I. Peretto, Drug Discov. Today 13 (2008) 677-684.
[12] C. Hulme, V. Gore, Curr. Med. Chem. 10 (2003) 51-80.
[13] A.D. Elbein, R. Molyneux, Alkaloids, Chemical and Biological Perspectives; John Wiley & Sons, New York, (1987); Vol. 57.
[14] D. O’Hagan, Nat. Prod. Rep. 17 (2000) 435-446.
[15] J.W. Daly, T.F. Spande, H.M. Garraffo, J. Nat. Prod. 68 (2005) 1556-1557.
[16] P.S. Watson, B. Jiang, B. Scott, Org. Lett. 2 (2000) 3679-3681.
[17] S. Petit, J.P. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, J.L. Imbs, Eur. J. Med. Chem. 26 (1991) 19-32.
[18] Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, S.E. Webber, T. Hermann, D. Wall, Bioorg. Med. Chem. Lett. 17 (2007) 1206-1210.
[19] M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17 (2009) 625-633.
[20] H. Bin, A.M. Crider, J.P. Stables, Eur. J. Med. Chem. 36 (2001) 265-286.
[21] A.B. Beeler, R.S.V.S. Gadepalli, S. Steyn, N.Jr. Castagnoli, J.M. Rimoldi, Bioorg. Med. Chem. 11 (2003) 5229-5234.
[22] J.A. Deskus, J.R. Epperson, P.S. Charles, A.C. Joseph, P. Dextraze, J. Qian-Cutrone, Q. Gao, B. Ma, B.R. Beno, G.K. Mattson, T.F. Molski, R.G. Krause, M.T. Taber, N.J. Lodge, R.J. Mattson, Bioorg. Med. Chem. Lett. 17 (2007) 3099-3104.
[23] S.L. Gwaltney II, S.J. O’Connor, L.T.J. Nelson, G.M. Sullivan, H. Imade, W. Wang, L. Hasvold, Q. Li, J. Cohen, W.Z. Gu, S.K. Tahir, J. Bauch, K. Marsh, S.C. Ng, D.J. Frost, H. Zhang, S. Muchmore, C.G. Jakob, V. Stoll, C. Hutchins, S.H. Rosenberg, H.L. Sham, Bioorg. Med. Chem. Lett. 13 (2003) 1359-1362.
[24] S. Nara, R. Tanaka, J. Eishima, M. Hara, Y. Takahashi, S. Otaki, R.J. Foglesong, P.F. Hughes, S. Turkington, Y. Kanda, J. Med. Chem. 46 (2003) 2467-2473.
[25] L. Nallan, K.D. Bauer, P. Bendale, K. Rivas, K. Yokoyama, C.P. Hornéy, P.R. Pendyala, D. Floyd, L.J. Lombardo, D.K. Williams, A. Hamilton, S. Sebti, W.T. Windsor, P.C. Weber, F.S. Buckner, D. Chakrabarti, M. H. Gelb, W.C. Van Voorhis, J. Med. Chem. 48 (2005) 3704-3713.
[26] M. Von Itzstein, W.Y. Wu, G.B. Kok, M.S. Pegg, J.C. Dyason, B. Jin, T.V. Phan, M.L. Smythe, H.F. White, S.W. Oliver, P.M. Colman, J.N. Varghese, D.M. Ryan, J.M. Woods, R.C. Bethell, V.J. Hothman, J.M. Camreon, C.R. Penn, Nature 363 (1993) 418-423.
[27] C.U. Kim, W. Lew, M.A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M.S. Chen, D.B. Mendel, C.Y. Tai, W.G. Laver, R.C. Stevens, J. Am. Chem. Soc. 119 (1997) 681-690.
[28] P.E. Goss, M.A. Baker, J.P. Carver, J.W. Dennis, Clin. Cancer Res. 1 (1995) 935-944.
[29] Y. Nishimura, T. Satoh, H. Adachi, S. Kondo, T. Takeuchi, M. Azetaka, H. Fukuyasu, Y. Iizuka, J. Med. Chem. 40 (1997) 2626-2633.
[30] G.B. Karlsson, T.D. Butters, R.A. Dwek, F.M. Platt, J. Biol. Chem. 268 (1993) 570-576.
[31] J.L. Treadway, P. Mendys, D.J. Hoover, Expert. Opin. Invest. Drugs 10 (2001) 439-454.
[32] P.A. Clarke, A.V. Zaytzev, A.C. Whitwood, Tetrahedron Lett. 48 (2007) 5209-5212.
[33] P.A. Clarke, A.V. Zaytzev, A.C. Whitwood, Synthesis (2008) 3530-3532.
[34] A.T. Khan, M. Lal, M.M. Khan, Tetrahedron Lett. 51 (2010) 4419-4424.
[35] A.T. Khan, T. Parvin, L.H. Choudhury, J. Org. Chem. 73 (2008) 8398-8402.
[36] H.-J. Wang, L.-P. Mo, Z.-H. Zhang, ACS Comb. Sci. 13 (2011) 181-185.
[37] A.T. Khan, M.M. Khan, K.K.R. Bannuru, Tetrahedron 66 (2010) 7762-7772.
[38] S. Mishra, R. Ghosh, Tetrahedron Lett. 52 (2011) 2857-2861.
[39] S. Pal, L.H. Choudhury, T. Parvin, Mol. Divers. 16 (2012) 129-143.
[40] G. Brahamachari, S. Das, Tetrahedron Lett. 53 (2012) 1479-1484.
[41] R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68 (2012) 363-369.
[42] B. Umamahesh, V. Sathesh, G. Ramachandran, M. Sathishkumar, K. Sathiyanarayanan, Catal. Lett. 142 (2012) 895-900.
[43] M.R.M. Shafiee, B.H. Najafabadi, M. Ghashang, J. Chem. Res. 36 (2012) 336-339.
[44] M. Ghashang, Lett. Org. Chem. 9 (2012) 497-502.
[45] M.R.M. Shafiee, B.H. Najafabadi, M. Ghashang, Res. Chem. Intermed. 39 (2013) 3753-3762.
[46] J. Cornil, A. Guérinot, S. Reymond, J. Cossy, J. Org. Chem. 78 (2013) 10273-10287.
[47] K. Komura, A. Ozaki, N. Ieda, Y. Sugi, Synthesis (2008) 3407-3410.
[48] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.J. Shams-Najafi, Monatsh. Chem. 143 (2012) 939-945.
[49] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, A.C. Willis, Chin. Chem. Lett. 23 (2012) 569-572.
[50] M.R. Mousavi, J. Aboonajmi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, M. Safarzaei, Lett. Org. Chem. 10 (2013) 171-177.
[51] J. Aboonajmi, M.R. Mousavi, M.T. Maghsoodlou, N. Hazeri, A. Masoumnia, Res. Chem. Intermed. DOI 10.1007/s11164-013-1320-z.
[52] N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Aboonajmi, S.S. Sajadikhah, J. Chin. Chem. Soc. 60 (2013) 355-358.
[53] M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, R. Doostmohamadi, Synth. Commun. 43 (2013) 635-644.
[54] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, M. Lashkari, J. Chem. Res. 36 (2012) 463-467.