Improved yields and more shortened reaction times were described for the conversion of 6-BrTHQ and 6,8-diBrTHQ into 6-bromoquinoline and 6,8-dibromoquinoline.
📌 3 Key Takeaways
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Objective & Hypothesis:In this study, bromination reactions of 1,2,3,4-tetrahydroquinoline by molecular bromine and aromatization reactions of brominated tetrahydroquinolines were reinvestigated.
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Key Findings & Data:Optimal reaction conditions were established for 6-Bromo-1,2,3,4-tetrahydroquinoline (6-BrTHQ ) and 6,8-dibromo-1,2,3,4-tetrahydroquinoline (6,8-diBrTHQ).
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Conclusion & Impact:Improved yields and more shortened reaction times were described for the conversion of 6-BrTHQ and 6,8-diBrTHQ into 6-bromoquinoline and 6,8-dibromoquinoline.
In this study, bromination reactions of 1,2,3,4-tetrahydroquinoline by molecular bromine and aromatization reactions of brominated tetrahydroquinolines were reinvestigated. Optimal reaction conditions were established for 6-Bromo-1,2,3,4-tetrahydroquinoline (6-BrTHQ ) and 6,8-dibromo-1,2,3,4-tetrahydroquinoline (6,8-diBrTHQ). Improved yields and more shortened reaction times were described for the conversion of 6-BrTHQ and 6,8-diBrTHQ into 6-bromoquinoline and 6,8-dibromoquinoline.
Kirsch, R., Kleim, J. P., Ries, G., Rosenstock, B., Roesner, M., Winkler, I. DE Patent 19,613,591, (1997)
Srivastava, S. K., Chauhan, P. M. S., Bhaduri, A. P., Fatima, N., Chatterjee, R. J. Med. Chem., 43, 2275, (2000)
Desai, P. K., Desai, P., Machhi, D., Desai, C. M., Patel, D. Indian J. Chem. Sect. B, 35(B), 871, (1996)
Muscia, G. C., Bollini, M., Carnevale, J. P., Bruno, A. M., Asis, S. E. Tetrahedron Lett., 47, 8811, (2006)
Agarwal, A. K., Jenekhe, S. A. Macromolecules, 24, 6806 (1991)
Zhang, X., Shetty, A. S., Jenekhe, S. A. Macromolecules, 32, 7422 (1999)
Zhang, N., Wu, B.,Powell, D., Wissner, A., Floyd, M.B., Kovacs, E.D., Toral-Barza, L., Kohler, C. Bioorg. Med. Chem. Lett., 10, 2825-2828, (2000)
Jenekhe, S. A., Lu, L., Alam, M. M. Macromolecules, 34, 7315. (2001)
Solomon, V. R., Lee, H. Eur. J. Pharmacol., 625, 220, (2009)
Boschelli, D.H., Wang, D.Y., Ye, F., Wu, B., Zhang, N., Dutia, M., Powell D. W., Wissner, A., Arndt, K., Weber, J.M., Boschelli, J. Med. Chem., 44, 822-833, (2001)
Company of a Chemistry Partner of Drug Discovery “BioBloks inc.”, 2002, San Diego, CA, USA. http://www.bioblocks.com/quinolines.html, [Erişim tarihi; 26 Şubat 2014]
Şahin, A., Çakmak, O., Demirtaş, İ., Ökten, S., Tutar, A., Tetrahedron, 64 (43), 10068-10074 (2008)
Ökten, S, Çakmak O, Erenler R, Tekin Ş, Yüce Ö., Turk. J. Chem. 37, 896-908 (2013).