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Decarboxylative Aromatization of b-Carbolines by Using Metal Free Catalysis and Efficient Synthesis of b-Carboline Derivatives
Corresponding Author(s) : Chunduru Srinivasa Rao
Asian Journal of Chemistry,
Vol. 27 No. 12 (2015): Vol 27 Issue 12
Abstract
A new novel metal-free decarboxylative and aromatized b-carboline (5a-j) derivatives were synthesized by one-pot reaction. In all cases, resulting b-carboline derivatives with above 90 % yield.
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- P.D. Bailey, P.J. Cochrane, A.H. Förster, K.M. Morgan and D.P.J. Pearson, Tetrahedron Lett., 40, 4597 (1999); doi:10.1016/S0040-4039(99)00735-2.
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- R. Meesala, M. Ezzat, M. Mordi and S. Mansor, Synlett, 25, 2176 (2014); doi:10.1055/s-0034-1378518.
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References
P.D. Bailey, P.J. Cochrane, A.H. Förster, K.M. Morgan and D.P.J. Pearson, Tetrahedron Lett., 40, 4597 (1999); doi:10.1016/S0040-4039(99)00735-2.
W. Meissner, J. Chem. Phys., 25, 377 (1819).
E.J. Massaro, Handbook of Neurotoxicology; Humana Press: Totowa, NJ, USA, p. 237 (2002).
J.C. Callaway, D.J. McKenna, C.S. Grob, G.S. Brito, L.P. Raymon, R.E. Poland, E.N. Andrade, E.O. Andrade and D.C. Mash, J. Ethnopharmacol., 65, 243 (1999); doi:10.1016/S0378-8741(98)00168-8.
J. Reniers, S. Robert, R. Frederick, B. Masereel, S. Vincent and J. Wouters, Bioorg. Med. Chem., 19, 134 (2011); doi:10.1016/j.bmc.2010.11.041.
S.K. Srivastava, A. Agarwal, P.M.S. Chauhan, S.K. Agarwal, A.P. Bhaduri, S.N. Singh, N. Fatima and R.K. Chatterjee, J. Med. Chem., 42, 1667 (1999); doi:10.1021/jm9800705.
J.G. Tang, Y.H. Wang, R.R. Wang, Z.J. Dong, L.M. Yang, Y.T. Zheng and J.K. Liu, Chem. Biodivers., 5, 447 (2008); doi:10.1002/cbdv.200890044.
J.F. Miller, E.M. Turner, R.G. Sherrill, K. Gudmundsson, A. Spaltenstein, P. Sethna, K.W. Brown, R. Harvey, K.R. Romines and P. Golden, Bioorg. Med. Chem. Lett., 20, 256 (2010); doi:10.1016/j.bmcl.2009.10.123.
N. Lin, M. Zhao, C. Wang and S. Peng, Bioorg. Med. Chem. Lett., 12, 585 (2002); doi:10.1016/S0960-894X(01)00809-5.
A. Batch and R.H. Dodd, J. Org. Chem., 63, 872 (1998); doi:10.1021/jo971485l.
H. Guan, H. Chen, W. Peng, Y. Ma, R. Cao, X. Liu and A. Xu, Eur. J. Med. Chem., 41, 1167 (2006); doi:10.1016/j.ejmech.2006.05.004.
J. Ishida, H.K. Wang, M. Oyama, M.L. Cosentino, C.Q. Hu and K.H. Lee, J. Nat. Prod., 64, 958 (2001); doi:10.1021/np0101189.
Y. Song, J. Wang, S.F. Teng, D. Kesuma, Y. Deng, J. Duan, J.H. Wang, R.Z. Qi and M.M. Sim, Bioorg. Med. Chem. Lett., 12, 1129 (2002); doi:10.1016/S0960-894X(02)00094-X.
Y. Song, D. Kesuma, J. Wang, Y. Deng, J. Duan, J.H. Wang and R.Z. Qi, Biochem. Biophys. Res. Commun., 317, 128 (2004); doi:10.1016/j.bbrc.2004.03.019.
A.M. Deveau, M.A. Labroli, C.M. Dieckhaus, M.T. Barthen, K.S. Smith and T.L. MacDonald, Bioorg. Med. Chem. Lett., 11, 1251 (2001); doi:10.1016/S0960-894X(01)00136-6.
A.C. Castro, L.C. Dang, F. Soucy, L. Grenier, H. Mazdiyasni, M. Hottelet, L. Parent, C. Pien, V. Palombella and J. Adams, Bioorg. Med. Chem. Lett., 13, 2419 (2003); doi:10.1016/S0960-894X(03)00408-6.
D.G. Harvey and W. Robson, J. Chem. Soc., 97 (1938); doi:10.1039/jr9380000097.
Q. Wu, R. Cao, M. Feng, X. Guan, C. Ma, J. Liu, H. Song and W. Peng, Eur. J. Med. Chem., 44, 533 (2009); doi:10.1016/j.ejmech.2008.03.030.
B. Xin, W. Tang, Y. Wang, G. Lin, H. Liu, Y. Jiao, Y. Zhu, H. Yuan, Y. Chen and T. Lu, Bioorg. Med. Chem. Lett., 22, 4783 (2012); doi:10.1016/j.bmcl.2012.05.053.
M.-L. Yang, P.-C. Kuo, T.-L. Hwang, W.-F. Chiou, K. Qian, C.-Y. Lai, K.-H. Lee and T.-S. Wu, Bioorg. Med. Chem., 19, 1674 (2011); doi:10.1016/j.bmc.2011.01.034.
R. Meesala, M. Ezzat, M. Mordi and S. Mansor, Synlett, 25, 2176 (2014); doi:10.1055/s-0034-1378518.
W. Huang, J. Li and L. Ou, Synth. Commun., 37, 2137 (2007); doi:10.1080/00397910701392459.
T.H. Tomico, J.G. Ochaita and C.C. Ronda, Preparation of b-Carboline from Natural Products and Foods having Monoaminooxidase Inhibiting Activity, PCT Int. Appl., 2007085679 (2007).