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Iron Powder Promoted Regio-Selective Friedel-Crafts Acylation of Indole Under Solvent-Free Conditions
Corresponding Author(s) : Fengping Yi
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
A facile, efficient and environment-friendly protocol for the regioselective synthesis of 3-acyl indoles has been developed by one-pot catalytic Friedel-Crafts acylation of indole in presence of the iron powder as catalyst under solvent-free conditions at room temperature.
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References
G. La Regina, T. Sarkar, R. Bai, M.C. Edler, R. Saletti, A. Coluccia, F. Piscitelli, L. Minelli, V. Gatti and C. Mazzoccoli, J. Med. Chem., 52, 7512 (2009).
Y.S. Wu, M.S. Coumar, J.Y. Chang, H.Y. Sun, F.M. Kuo, C.C. Kuo, Y.J. Chen, C.Y. Chang, C.L. Hsiao and J.P. Liou, J. Med. Chem., 52, 4941 (2009).
S.C. Eyley, R.G. Giles and H. Heaney, Tetrahedron Lett., 26, 4649 (1985).
J. Bergman and L. Venemalm, Tetrahedron Lett., 28, 3741 (1987).
M.M. Faul and L.L. Winneroski, Tetrahedron Lett., 38, 4749 (1997).
K.S. Yeung, M.E. Farkas, Z. Qiu and Z. Yang, Tetrahedron Lett., 43, 5793 (2002).
O. Ottoni, A.D.F. Neder, A.K.B. Dias, R.P.A. Cruz and L.B. Aquino, Org. Lett., 3, 1005 (2001).
J.H. Wynne, C.T. Lloyd, S.D. Jensen, S. Boson and W.M. Stalick, Synthesis, 2277 (2004).
T. Okauchi, M. Itonaga, T. Minami, T. Owa, K. Kitch and H. Yoshino, Org. Lett., 2, 1485 (2000).
K.S. Yeung, Z. Qiu, M.E. Farkas, Q. Xue, A. Regueiro-Ren, Z. Yang, J.A. Bender, A.C. Good and J.F. Kadow, Tetrahedron Lett., 49, 6250 (2008).
D.M. Ketcha and G.W. Gribble, J. Org. Chem., 50, 5451 (1985).
T. Watanabe, A. Kobayashi, M. Nishiura, H. Takahashi, T. Usui, I. Kamiyama, N. Mochizuki, K. Noritake, Y. Yokoyama and Y. Murakami, Chem. Pharm. Bull., 39, 1152 (1991).
S.K. Guchhait, M. Kashyap and H. Kamble, J. Org. Chem., 76, 4753 (2011).
J.O. Morley, J. Chem. Soc. Perkin Trans. II, 601 (1977).
S. Paul, P. Nand, R. Gupta and A. Loupy, Synthesis, 2877 (2003).
M.H. Sarvari and H. Sharghi, J. Org. Chem., 69, 6953 (2004).