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Novel Commercial Scale Synthetic Approach for 5-Cyanoindole: A Potential Intermediate for Vilazodone Hydrochloride, an Antidepressant Drug
Corresponding Author(s) : M. Venkatanarayana
Asian Journal of Chemistry,
Vol. 32 No. 10 (2020): Vol 32 Issue 10
Abstract
Present work describes the synthesis of 5-cyanoindole, a common intermediate used in various synthetic route of the antidepressant vilazodone hydrochloride. The protocol is both robust and commercially viable, utilizing readily available and low-cost materials and the isomers are environmental friendly than previously reported routes through its evading use of cyanide reagents and heavy metals.
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- J. Lovas, R.D. Suenram, G.T. Fraser, C.W. Gillies and J. Zozom, J. Chem. Phys., 88, 722 (1988); https://doi.org/10.1063/1.454151
- Y. Yovel, M.O. Franz, P. Stilz and H.-U. Schnitzler, PLoS Comput. Biol., 4, e1000032 (2008); https://doi.org/10.1371/journal.pcbi.1000032
- H. Abdel-Gawad, H.A. Mohamed, K.M. Dawood and F.A.-R. Badria, Heterocycl. Chem. Pharm. Bull., 58, 1529 (2010); https://doi.org/10.1248/cpb.58.1529
- M.M. Heravi, S. Rohani, V. Zadsirjan and N. Zahedi, RSC Adv., 7, 52852 (2017); https://doi.org/10.1039/C7RA10716A
- J. Chen, Z. Zhang, S. Liu, C. Yang and C. Xia, RSC Adv., 4, 4672 (2014); https://doi.org/10.1039/C3RA45548C
- H. Yu, R.N. Richey, W.D. Miller, J. Xu and S.A. May, J. Org. Chem., 76, 665 (2011); https://doi.org/10.1021/jo102037y
- C. Saá, A. Varela-Fernández and J. Varela, Synthesis, 44, 3285 (2012); https://doi.org/10.1055/s-0032-1316539
- J. Zanon, A. Klapars and J. Buchwald, J. Am. Chem. Soc., 125, 2890 (2003); https://doi.org/10.1021/ja0299708
- N. Anitha, B.S. Reddy, N.M. Sekhar, K.V. Reddy and E.R.R. Chandrasekhar, Synth. Commun., 44, 3563 (2014); https://doi.org/10.1080/00397911.2014.944268
- Z.M. Mao, J. Dongxu and S. Xiang, Preparation of 5-Cyanoindole. Chinese Patent CN110396059A (2019).
- C. Battilocchio, J.M. Hawkins and S.V. Ley, Org. Lett., 16, 1060 (2014); https://doi.org/10.1021/ol403591c
References
J. Lovas, R.D. Suenram, G.T. Fraser, C.W. Gillies and J. Zozom, J. Chem. Phys., 88, 722 (1988); https://doi.org/10.1063/1.454151
Y. Yovel, M.O. Franz, P. Stilz and H.-U. Schnitzler, PLoS Comput. Biol., 4, e1000032 (2008); https://doi.org/10.1371/journal.pcbi.1000032
H. Abdel-Gawad, H.A. Mohamed, K.M. Dawood and F.A.-R. Badria, Heterocycl. Chem. Pharm. Bull., 58, 1529 (2010); https://doi.org/10.1248/cpb.58.1529
M.M. Heravi, S. Rohani, V. Zadsirjan and N. Zahedi, RSC Adv., 7, 52852 (2017); https://doi.org/10.1039/C7RA10716A
J. Chen, Z. Zhang, S. Liu, C. Yang and C. Xia, RSC Adv., 4, 4672 (2014); https://doi.org/10.1039/C3RA45548C
H. Yu, R.N. Richey, W.D. Miller, J. Xu and S.A. May, J. Org. Chem., 76, 665 (2011); https://doi.org/10.1021/jo102037y
C. Saá, A. Varela-Fernández and J. Varela, Synthesis, 44, 3285 (2012); https://doi.org/10.1055/s-0032-1316539
J. Zanon, A. Klapars and J. Buchwald, J. Am. Chem. Soc., 125, 2890 (2003); https://doi.org/10.1021/ja0299708
N. Anitha, B.S. Reddy, N.M. Sekhar, K.V. Reddy and E.R.R. Chandrasekhar, Synth. Commun., 44, 3563 (2014); https://doi.org/10.1080/00397911.2014.944268
Z.M. Mao, J. Dongxu and S. Xiang, Preparation of 5-Cyanoindole. Chinese Patent CN110396059A (2019).
C. Battilocchio, J.M. Hawkins and S.V. Ley, Org. Lett., 16, 1060 (2014); https://doi.org/10.1021/ol403591c