Selective and efficient synthesis of 3-indolyl-2-oxindoles under catalysis of LiClO4
محورهای موضوعی : Iranian Journal of CatalysisKurosh Rad-Moghadam 1 , Shaghayegh Gholizadeh 2
1 - Chemistry Department, University of Guilan, P.O. Box 41335-19141, Rasht, Iran.
2 - Chemistry Department, , Tonekabon Branch, Islamic Azad University Tonekabon, Iran.
کلید واژه: Lithium perchlorate, 3-hydroxy-3-indolyl-2-oxindole, 3, 3-diindolyl-2-oxindole, Selective synthesis,
چکیده مقاله :
An efficient and convenient protocol for synthesis of 3-hydroxy-3-indolyl-2-oxindoles and 3,3-diindolyl-2-oxindoles is presented here. The syntheses were achieved selectively under catalysis of LiClO4 whereby the products were obtained purely.
1] R.J. Sundberg, D.J. Faulkner, I.J. Ninomiya, Nat. Prod., 55 (1992) 541-547.
[2] K.C. Joshi, V.N. Pathak, H. Pajouhesh, Heterocycl. Chem., 21 (1984) 1641-1646.
[3] F. Garrido, J. Ibanez, E. Gonalons, A. Giraldez, Eur. J. Med. Chem., 47 (2004) 1882-1889.
[4] A. Natarajan, Y. Fan, H. Chen, Y. Guo, J. Iyasere, F. Harbinski, W.J. Christ, J.A. Halperin, J. Med. Chem., 47 (2004) 1884-1890.
[5] T. Osawa, M. Namiki, Tetrahedron Lett., 29 (1983) 4719-4723.
[6] C. Hong, G. L Firestone, L. F. Bjeldanes, Biochem. Pharmacol., 63 (2002) 1085-1089.
[7] T. Ratan Bal, B. Anand, P. Yogeeswari, Bioorg. Med. Chem. Lett., 15 (2005) 4451-4455.
[8] T. Jiang, K.L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Tuntland, K. Zhang, Bioorg. Med. Chem. Lett., 16 (2006) 2109-2112.
[9] R. Tripathy, A. Reiboldt, P.A. Messina, M. Iqbal, J. Singh, E.R. Bacon, Th.S. Angeles, Bioorg. Med. Chem. Lett., 10 (2006) 2158-2162.
[10] A. Cane, M.C. Tournaire, D. Barritault, M. Crumeyrolle-Arias, Biochem. Biophys. Res. Commun., 276 (2000) 379-384.
[11] V.C. Silveira, J.S. Luz, C.C. Oliveira, I. Graziani, M.R. Ciriolo, A.M. Costa. Ferreira, J. Inorg. Biochem., 102 (2008) 1090-1103.
[12] A. Amal Raj, R. Raghunathan, M.R. Sridevikumaria, N. Raman, Bioorg. Med. Chem., 11 (2003) 407-419.
[13] M.C. Rodriguez-Arguelles, S. Mosquera-Vazaquez, P. Touron-Touceda, J. Sanmar-Matalobos, A.M. Garcia-Deibe, C. Pelizzi, Inorg. Biochem., 101 (2007) 138-147.
[14] L. Maskell, E.A. Blanche, M.A. Colucci, J.L. Whatmore, Bioorg. Med. Chem. Lett., 17 (2007) 1575-1578.
[15] M. Verma, S. NathPandeya, K. Nand Singh, J.P. Stables, Acta Pharm., 54 (2004) 49-56.
[16] N. Igosheva, C. Lorz, E. O´Conner, V. Glover, H. Mehmet, Neurochem. Int., 47 (2005) 216-224.
[17] L.R. Chen, Y.C. Wang, Y.W. lin, S.Y. Chou, S.F. Chen, L.T. Liu, Y.T. Wu, C.J. Kuo, Bioorg. Med. Chem. Lett., 15 (2005) 3058-3062.
[18] R. Shimazawa, M. Kuriyama, R. Shirai, Bioorg. Med. Chem. Lett., 18 (2008) 3350-3353.
[19] Y. Wu, M. Kitajima, N. Kogure, R. Zhang, H. Takayama. Tetrahedron Lett., 49 (2008) 5935-5938.
[20] B.S. Jursic, E.D. Stevens, Tetrahedron Lett., 43 (2002) 5681-5683.
[21] D.A. Klurapp, K.Y. Yeung, G.K.S. Prakash, G.A. Olah, J. Org. Chem., 63 (1998) 4481-4484.
[22] I. Sharma, A. Saxena, C.K. Ojha, C.K.P. Paradasani, R.T. Paradasani, T. Mukherjee Proc, Indian Acad. Chem. Sci., 114 (2002) 523-531.
[23] S.P. Marsden, E.L. Watson, S.A. Raw, Org. Lett., 10 (2008) 2905-2908.
[24] F.X. Felpin, O. Ibarguren, L. Nassar-Hardy, F. Fouquet, J. Org. Chem., 74 (2009) 1349-1352.
[25] G. Luppi, P.G. Cozzi, M. Monari, B. Kaptein, Q.B. Broxterman, C. Tomasini, J. Org. Chem., 70 (2005) 7418-7421.
[26] A.V. Malkov, M.A. Kabeshov, M. Bella, O. Kysilka, D.A. Malyshev, K. Pluhackova, P. Kocovsky, Org. Lett., 9 (2007) 5473-5476.
[27] J. Azizian, A.A. Mohammadi, N. Karimi, M.R. Mohammadizadeh, A.R. Karimi, Catal. Commun., 7 (2006) 752-755.
[28] S.Y. Wang, S.J. Ji, Tetrahedron, 62 (2006) 1527-1535.
[29] C. Ganachaud, V. Garfagnoli, T. Tron, G. Iacazio, Tetrahedron Lett., 49 (2008) 2476-2478.
[30] A. Frechard, N. Fabre, C. Pean, S. Mantaut, M.T. Fauvel, P. Rollin, I. Fouraste, Tetrahedron Lett., 42 (2001) 9015-9017.
[31] Y.Q. Tang, I. Sattler, R. Thiericke, S. Grabley. J. Org. Chem., 49 (2001) 261-267.
[32] N. Madhavan, C.W. Jones, M. Weck, Acc. Chem. Res., 41 (2008) 1153-1165.
[33] G. Shanthi, N. Lakshmi, P.T. Perumal, Arkivoc, X (2009) 121-130.
[34] K. Rad-Moghadam, M. Sharifi-Kiasaraie, H. Taheri-Amlashi, Tetrahedron, 66 (2010) 2316-2321.
[35] P. Paira, A. Hazra, S. Kumar, R. Paira, K.B. Sahu, S. Naskar, P. Saha, S. Mondal, A. Maity, S. Banerjee, N.B. Mondal, Bioorg. Med. Chem. Lett., 19 (2009) 4786–4789.
[36] B.V. Subba Reddy, N. Rajeswari, M. Sarangapani, Y. Prashanthi, R. J. Ganji, A. Addlagatta, Bioorg. Med. Chem. Lett., 22 (2012) 2460-2463.
