SYNTHESIS OF BROMINATED QUINOLINES

Year 2015, Volume: 33 Issue: 1, 8 - 15, 01.03.2015

Salih Ökten Dilek Eyigün Osman Çakmak

Abstract

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.

Keywords

Quinoline, tetrahydroquinoline, bromoquinoline, bromination, aromatization, DDQ

References

• [1] Kirsch, R., Kleim, J. P., Ries, G., Rosenstock, B., Roesner, M., Winkler, I. DE Patent 19,613,591, (1997).
• [2] Srivastava, S. K., Chauhan, P. M. S., Bhaduri, A. P., Fatima, N., Chatterjee, R. J. Med. Chem., 43, 2275, (2000).
• [3] Desai, P. K., Desai, P., Machhi, D., Desai, C. M., Patel, D. Indian J. Chem. Sect. B, 35(B), 871, (1996).
• [4] Muscia, G. C., Bollini, M., Carnevale, J. P., Bruno, A. M., Asis, S. E. Tetrahedron Lett., 47, 8811, (2006).
• [5] Agarwal, A. K., Jenekhe, S. A. Macromolecules, 24, 6806 (1991).
• [6] Zhang, X., Shetty, A. S., Jenekhe, S. A. Macromolecules, 32, 7422 (1999).
• [7] 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).
• [8] Jenekhe, S. A., Lu, L., Alam, M. M. Macromolecules, 34, 7315. (2001).
• [9] Solomon, V. R., Lee, H. Eur. J. Pharmacol., 625, 220, (2009).
• [10] 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).
• [11] 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].
• [12] Şahin, A., Çakmak, O., Demirtaş, İ., Ökten, S., Tutar, A., Tetrahedron, 64 (43), 10068-10074 (2008).
• [13] Ökten, S, Çakmak O, Erenler R, Tekin Ş, Yüce Ö., Turk. J. Chem. 37, 896-908 (2013).