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NbCl5 and AgClO4 Promoted Regio-Selective Acylation of Indoles
Corresponding Author(s) : Narendra R. Kamble
Asian Journal of Chemistry,
Vol. 32 No. 2 (2020): Vol 32 Issue 2
Abstract
In present study, an efficient and simple strategy towards chemo-selective and regio-selective acylation of indole using NbCl5 and AgClO4 catalyst are reported. This method utilizes the catalytic potentiality of NbCl5 and AgClO4 towards acylation of unprotected indoles in a synergistic manner. The combination of these catalytic system results into numerous advantages such as excellent yields of product, short reaction times and easier isolation of products.
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- M.M. Faul, L.L. Winneroski and C.A. Krumrich, J. Org. Chem., 63, 6053 (1998); https://doi.org/10.1021/jo980513c.
- P.M. Fresneda, P. Molina and M. Angeles Saez, Synlett, 1651 (1999); https://doi.org/10.1055/s-1999-2903.
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- R.J. Sundberg, Indoles; Academic Press: New York, p. 105 (1996).
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- T. Okauchi, M. Itonaga, T. Minami, T. Owa, K. Kitoh and H. Yoshino, Org. Lett., 2, 1485 (2000); https://doi.org/10.1021/ol005841p.
- J.H. Wynne, C.T. Lloyd, S.D. Jensen, S. Boson and W.M. Stalick, Synthesis, 2277 (2004); https://doi.org/10.1055/s-2004-831177.
- O. Ottoni, A.V. Neder, A.K.B. Dias, R.P.A. Cruz and L.B. Aquino, Org. Lett., 3, 1005 (2001); https://doi.org/10.1021/ol007056i.
- D.M. Ketcha and G.W. Gribble, J. Org. Chem., 50, 5451 (1985); https://doi.org/10.1021/jo00350a001.
- 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); https://doi.org/10.1016/j.tetlet.2008.08.045.
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- J. Bergman, J.-E. backvall and J.-O. Lindström, Tetrahedron, 29, 971 (1973); https://doi.org/10.1016/0040-4020(73)80047-X.
- W. Anthony, J. Org. Chem., 25, 2049 (1960); https://doi.org/10.1021/jo01081a615.
- J. Bergman and L. Venemalm, Tetrahedron Lett., 28, 3741 (1987); https://doi.org/10.1016/S0040-4039(00)96373-1.
- M.M. Faul and L.L. Winneroski, Tetrahedron Lett., 38, 4749 (1997); https://doi.org/10.1016/S0040-4039(97)01028-9.
- S.C. Eyley, R.G. Giles and H. Heaney, Tetrahedron Lett., 26, 4649 (1985); https://doi.org/10.1016/S0040-4039(00)98776-8.
- A.R. Katritzky, K. Suzuki, S.K. Singh and H.Y. He, J. Org. Chem., 68, 5720 (2003); https://doi.org/10.1021/jo034187z.
- J.E. Taylor, M.D. Jones, J.M.J. Williams and S.D. Bull, Org. Lett., 12, 5740 (2010); https://doi.org/10.1021/ol1025348.
- J.E. Huheey, Inorganic Chemistry: Principles of Structure and Reactivity, Harper & Row: Singapore, edn 3 (1990).
- R.J. Lewis and S.R. Dangerous Properties of Industrial Materials, Van Nostrand Reinhold: New York, edn 8, p. 3 (1989).
- H. Maeta, T. Nagasawa, Y. Handa, T. Takei, Y. Osamura and K. Suzuki, Tetrahedron Lett., 36, 899 (1995); https://doi.org/10.1016/0040-4039(94)02332-6.
- Q. Guo, T. Miyaji, R. Hara, B. Shen and T. Takahashi, Tetrahedron, 58, 7327 (2002); https://doi.org/10.1016/S0040-4020(02)00738-X.
- K. Suzuki, T. Hashimoto, H. Maeta and T. Matsumoto, Synlett, 125 (1992); https://doi.org/10.1055/s-1992-21288.
- S. Arai, A. Nishida and Y. Sudo, Synlett, 1104 (2004); https://doi.org/10.1055/s-2004-817766.
- G.A. Olah, Friedel-Crafts Chemistry; Wiley-Interscience: London (1973).
- S. Kobayashi and S. Iwamoto, Tetrahedron Lett., 39, 4697 (1998); https://doi.org/10.1016/S0040-4039(98)00881-8.
- A. Kawada, S. Mitamura, J.I. Matsuo, T. Tsuchiya and S. Kobayashi, Bull. Chem. Soc. Jpn., 73, 2325 (2000); https://doi.org/10.1246/bcsj.73.2325.
- N.R. Kamble and V.T. Kamble, Asian J. Chem., 31, 1357 (2019); https://doi.org/10.14233/ajchem.2019.21986.
References
M.M. Faul, L.L. Winneroski and C.A. Krumrich, J. Org. Chem., 63, 6053 (1998); https://doi.org/10.1021/jo980513c.
P.M. Fresneda, P. Molina and M. Angeles Saez, Synlett, 1651 (1999); https://doi.org/10.1055/s-1999-2903.
G. La Regina, T. Sarkar, R. Bai, M.C. Edler, R. Saletti, A. Coluccia, F. Piscitelli, L. Minelli, V. Gatti, C. Mazzoccoli, V. Palermo, C. Mazzoni, C. Falcone, A.I. Scovassi, V. Giansanti, P. Campiglia, A. Porta, B. Maresca, E. Hamel, A. Brancale, E. Novellino and R. Silvestri, J. Med. Chem., 52, 7512 (2009); https://doi.org/10.1021/jm900016t.
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, J.P. Liou, C.P. Chen, H.T. Yao, Y.K. Chiang, U.K. Tan, C.T. Chen, C.Y. Chu, S.Y. Wu, T.K. Yeh, C.Y. Lin and H.P. Hsieh, J. Med. Chem., 52, 4941 (2009); https://doi.org/10.1021/jm900060s.
I. Nicolaou and V.J. Demopoulos, J. Med. Chem., 46, 417 (2003); https://doi.org/10.1021/jm0209477.
M.L. Barreca, S. Ferro, A. Rao, L. De Luca, M. Zappalà, A.M. Monforte, Z. Debyser, M. Witvrouw and A. Chimirri, J. Med. Chem., 48, 7084 (2005); https://doi.org/10.1021/jm050549e.
R.J. Sundberg, Indoles; Academic Press: New York, p. 105 (1996).
K.S. Yeung, M.E. Farkas, Z. Qiu and Z. Yang, Tetrahedron Lett., 43, 5793 (2002); https://doi.org/10.1016/S0040-4039(02)01185-1.
T. Okauchi, M. Itonaga, T. Minami, T. Owa, K. Kitoh and H. Yoshino, Org. Lett., 2, 1485 (2000); https://doi.org/10.1021/ol005841p.
J.H. Wynne, C.T. Lloyd, S.D. Jensen, S. Boson and W.M. Stalick, Synthesis, 2277 (2004); https://doi.org/10.1055/s-2004-831177.
O. Ottoni, A.V. Neder, A.K.B. Dias, R.P.A. Cruz and L.B. Aquino, Org. Lett., 3, 1005 (2001); https://doi.org/10.1021/ol007056i.
D.M. Ketcha and G.W. Gribble, J. Org. Chem., 50, 5451 (1985); https://doi.org/10.1021/jo00350a001.
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); https://doi.org/10.1016/j.tetlet.2008.08.045.
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); https://doi.org/10.1248/cpb.39.1152.
J. Bergman, J.-E. backvall and J.-O. Lindström, Tetrahedron, 29, 971 (1973); https://doi.org/10.1016/0040-4020(73)80047-X.
W. Anthony, J. Org. Chem., 25, 2049 (1960); https://doi.org/10.1021/jo01081a615.
J. Bergman and L. Venemalm, Tetrahedron Lett., 28, 3741 (1987); https://doi.org/10.1016/S0040-4039(00)96373-1.
M.M. Faul and L.L. Winneroski, Tetrahedron Lett., 38, 4749 (1997); https://doi.org/10.1016/S0040-4039(97)01028-9.
S.C. Eyley, R.G. Giles and H. Heaney, Tetrahedron Lett., 26, 4649 (1985); https://doi.org/10.1016/S0040-4039(00)98776-8.
A.R. Katritzky, K. Suzuki, S.K. Singh and H.Y. He, J. Org. Chem., 68, 5720 (2003); https://doi.org/10.1021/jo034187z.
J.E. Taylor, M.D. Jones, J.M.J. Williams and S.D. Bull, Org. Lett., 12, 5740 (2010); https://doi.org/10.1021/ol1025348.
J.E. Huheey, Inorganic Chemistry: Principles of Structure and Reactivity, Harper & Row: Singapore, edn 3 (1990).
R.J. Lewis and S.R. Dangerous Properties of Industrial Materials, Van Nostrand Reinhold: New York, edn 8, p. 3 (1989).
H. Maeta, T. Nagasawa, Y. Handa, T. Takei, Y. Osamura and K. Suzuki, Tetrahedron Lett., 36, 899 (1995); https://doi.org/10.1016/0040-4039(94)02332-6.
Q. Guo, T. Miyaji, R. Hara, B. Shen and T. Takahashi, Tetrahedron, 58, 7327 (2002); https://doi.org/10.1016/S0040-4020(02)00738-X.
K. Suzuki, T. Hashimoto, H. Maeta and T. Matsumoto, Synlett, 125 (1992); https://doi.org/10.1055/s-1992-21288.
S. Arai, A. Nishida and Y. Sudo, Synlett, 1104 (2004); https://doi.org/10.1055/s-2004-817766.
G.A. Olah, Friedel-Crafts Chemistry; Wiley-Interscience: London (1973).
S. Kobayashi and S. Iwamoto, Tetrahedron Lett., 39, 4697 (1998); https://doi.org/10.1016/S0040-4039(98)00881-8.
A. Kawada, S. Mitamura, J.I. Matsuo, T. Tsuchiya and S. Kobayashi, Bull. Chem. Soc. Jpn., 73, 2325 (2000); https://doi.org/10.1246/bcsj.73.2325.
N.R. Kamble and V.T. Kamble, Asian J. Chem., 31, 1357 (2019); https://doi.org/10.14233/ajchem.2019.21986.