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One-Pot, Water-Mediated, H2O2-HCl Catalyzed Synthesis of Benzazepines
Corresponding Author(s) : Jaya Pandey
Asian Journal of Chemistry,
Vol. 32 No. 5 (2020): Vol 32 Issue 5
Abstract
One-pot, multicomponent H2O2-HCl catalyzed system was employed for the synthesis of a series of benzazepine compounds. The implemented procedure oxidized the carbon-nitrogen bonds and produced benzazepines, while integrating diamines and substituted ketone. The advantage of the exercised synthetic route was that the reaction was water mediated and the completion time was quite reduced compared to the time required by conventional methods.
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- T.J. Dodds, Prim. Care Companion CNS Disord., 19, 16r02037 (2017); https://doi.org/10.4088/PCC.16r02037
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M.R. O’grady, M.L. O’sullivan, S.L. Minors and R. Horne, J. Vet. Intern. Med., 23, 977 (2009); https://doi.org/10.1111/j.1939-1676.2009.0346.x
J.N. King, C. Christinaz, G. Strehlau and J. Hornfeld, J. Vet. Pharmacol. Ther., 41, 485 (2018); https://doi.org/10.1111/jvp.12475
W.C. Oliver Jr., G.A. Nuttall, K.J. Cherry, P.A. Decker, T. Bower and M.H. Ereth, Anesth. Analg., 103, 833 (2006); https://doi.org/10.1213/01.ane.0000237273.79553.9e
S.W. Martin and K.J. Broadley, Br. J. Pharmacol., 115, 349 (1995); https://doi.org/10.1111/j.1476-5381.1995.tb15884.x
A.D. Medhurst, A.R. Atkins, I.J. Beresford, K. Brackenborough, M.A. Briggs, A.R. Calver, J. Cilia, J.E. Cluderay, B. Crook, J.B. Davis, R.K. Davis, R.P. Davis, L.A. Dawson, A.G. Foley, J. Gartlon, M.I. Gonzalez, T. Heslop, W.D. Hirst, C. Jennings, D.N.C. Jones, L.P. Lacroix, A. Martyn, S. Ociepka, A. Ray, C.M. Regan, J.C. Roberts, J. Schogger, E. Southam, T.O. Stean, B.K. Trail, N. Upton, G. Wadsworth, J.A. Wald, T. White, J. Witherington, M.L. Woolley, A. Worby and D.M. Wilson, J. Pharmacol. Exp. Ther., 321, 1032 (2007); https://doi.org/10.1124/jpet.107.120311
J.C. Kaski, S. Gloekler, R. Ferrari, K. Fox, B.I. Lévy, M. Komajda, P. Vardas and P.G. Camici, Open Heart, 5, e000725 (2018); https://doi.org/10.1136/openhrt-2017-000725
M. Volterrani and F. Iellamo, Card. Fail. Rev., 2, 63 (2016); https://doi.org/10.15420/cfr.2015:26:1
D.B. Brashier, A.K. Sharma, N. Dahiya, S.K. Singh and A. Khadka, J. Pharmacol. Pharmacother.,5, 175 (2014); https://doi.org/10.4103/0976-500X.130158
K. Fagerström and J. Hughes, Neuropsychiatr. Dis. Treat., 4, 353 (2008); https://doi.org/10.2147/NDT.S927
K. Yamaguchi, N. Shijubo, T. Kodama, K. Mori, T. Sugiura, T. Kuriyama, M. Kawahara, T. Shinkai, H. Iguchi and M. Sakurai, Jpn. J. Clin. Oncol., 41, 148 (2010); https://doi.org/10.1093/jjco/hyq170
T. Tamura and K. Takeuchi, BMJ Case Rep., 2013 bcr2013010039 (2013); https://doi.org/10.1136/bcr-2013-010039
R. Wang, R.X. Jin, Z.Y. Qin, K.J. Bian and X.S. Wang, Chem. Commun., 53, 12229 (2017); https://doi.org/10.1039/C7CC07027F
D. Li, Y. Park, W. Yoon, H. Yun and J. Yun, Organic Lett., 21, 9699 (2019); https://doi.org/10.1021/acs.orglett.9b03853
S.E. Feng, F. Xu and Q. Shen, Chin. J. Chem., 26, 1163 (2008); https://doi.org/10.1002/cjoc.200890213
J. Wu, F. Xu, Z. Zhou and Q. Shen, Synth. Commun., 36, 457 (2006); https://doi.org/10.1080/00397910500383527
L.Z. Yu, Q. Xu, X.Y. Tang and M. Shi, ACS Catal., 6, 526 (2016); https://doi.org/10.1021/acscatal.5b02400
A.K. Pandey, S.H. Han, N.K. Mishra, D. Kang, S.H. Lee, R. Chun, S. Hong, J.S. Park and I.S. Kim, ACS Catal., 8, 742 (2018); https://doi.org/10.1021/acscatal.7b03812
P.A. Donets and E.V. Van der Eycken, Org. Lett., 9, 3017 (2007); https://doi.org/10.1021/ol071079g
N. Bozinovic, I. Opsenica and B.A. Solaja, Synlett, 24, 49 (2013); https://doi.org/10.1055/s-0032-1317667
T.O. Vieira and H. Alper, Org. Lett., 10, 485 (2008); https://doi.org/10.1021/ol702933g
K. Bahrami, M.M. Khodaei and I. Kavianinia, J. Chem. Res., 2006, 783 (2006); https://doi.org/10.3184/030823406780199730