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Synthesis and Antibacterial Activities of Some Quinoline Substituted Quinoxaline Derivatives
Corresponding Author(s) : G. Anukumari
Asian Journal of Chemistry,
Vol. 27 No. 8 (2015): Vol 27 Issue 8
Abstract
p-Anisidine (1) on treatment with ethyl acetoacetate gave 1-(ethyl-3-[(4-methoxyphenyl)imino]butanoate) (2), which on cyclization in hot Dowtherm oil gave 4-hydroxy-6-methoxy-2-methylquinoline (3). The latter, on chlorination with SO2Cl2, gave 3-chloro-4-hydroxy-6-methoxy-2-methylquinoline (4) which with POCl3 was transformed into 3,4-dichloro-6-methoxy-2-methylquinoline (5). Treatment of compound 5 with o-phenylenediamine gave the novel product 2-methoxy-6-methyl-7,7a,11a,12-tetrahydroquinolino[3,4-b]quinoxaline (6) whose structure was assigned based on spectral data.
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- F.W. Muregi and A. Ishish, Drug Dev. Res., 71, 20 (2010); doi:10.1002/ddr.20345.
- A.-H. Li, E. Ahmed, X. Chen, M. Cox, A.P. Crew, H.-Q. Dong, M. Jin, L. Ma, B. Panicker, K.W. Siu, A.G. Steinig, K.M. Stolz, P.A.R. Tavares, B. Volk, Q. Weng, D. Werner and M.J. Mulvihill, J. Org. Biomol. Chem., 5, 61 (2006); doi:10.1039/b613775j.
- I.A. Mohammed and E. Subramanyam, Acta Pharm. Sci., 51, 163 (2009).
- E. Rajanarendar, M. Nagi Reddy, S. Rama Krishna, K. Rama Murthy, Y.N. Reddy and M.V. Rajam, J. Med. Chem., 55, 273 (2012); doi:10.1016/j.ejmech.2012.07.029.
- F. Hayat, A. Salahuddin and A. Azam, J. Enzyme Inhib. Med. Chem., 26, 472 (2010); doi:10.3109/14756366.2010.528414.
- M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada and A. Zilberstein, J. Med. Chem., 37, 2129 (1994); doi:10.1021/jm00040a003.
- D.R. Buckle, C.J.M. Rockell, H. Smith and B.A. Spicer, J. Med. Chem., 29, 2262 (1986); doi:10.1021/jm00161a022.
- M.P. LaMontagne, A. Markovac and M. Sami Khan, J. Med. Chem., 25, 964 (1982); doi:10.1021/jm00350a016.
- K. Kacprzak, Synlett, 943 (2005); doi:10.1055/s-2005-864809.
- J. Finnerty and H. Wentrup, J. Org. Chem., 70, 9735 (2005); doi:10.1021/jo051389h.
- H. Briehl, A. Lukosch and C. Wentrup, J. Org. Chem., 49, 2772 (1984); doi:10.1021/jo00189a025.
- A.L. Barry, in ed: V.L. Corian, Procedure for Testing Antimicrobial Agents in Agar Media, Antibiotics in Laboratory Medicine, Williams and Wilkins, Baltimore, MD (1980).
- K.D. Thomas, A.V. Adhikari and N.S. Shetty, Eur. J. Med. Chem., 45, 3803 (2010); doi:10.1016/j.ejmech.2010.05.030.
References
F.W. Muregi and A. Ishish, Drug Dev. Res., 71, 20 (2010); doi:10.1002/ddr.20345.
A.-H. Li, E. Ahmed, X. Chen, M. Cox, A.P. Crew, H.-Q. Dong, M. Jin, L. Ma, B. Panicker, K.W. Siu, A.G. Steinig, K.M. Stolz, P.A.R. Tavares, B. Volk, Q. Weng, D. Werner and M.J. Mulvihill, J. Org. Biomol. Chem., 5, 61 (2006); doi:10.1039/b613775j.
I.A. Mohammed and E. Subramanyam, Acta Pharm. Sci., 51, 163 (2009).
E. Rajanarendar, M. Nagi Reddy, S. Rama Krishna, K. Rama Murthy, Y.N. Reddy and M.V. Rajam, J. Med. Chem., 55, 273 (2012); doi:10.1016/j.ejmech.2012.07.029.
F. Hayat, A. Salahuddin and A. Azam, J. Enzyme Inhib. Med. Chem., 26, 472 (2010); doi:10.3109/14756366.2010.528414.
M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada and A. Zilberstein, J. Med. Chem., 37, 2129 (1994); doi:10.1021/jm00040a003.
D.R. Buckle, C.J.M. Rockell, H. Smith and B.A. Spicer, J. Med. Chem., 29, 2262 (1986); doi:10.1021/jm00161a022.
M.P. LaMontagne, A. Markovac and M. Sami Khan, J. Med. Chem., 25, 964 (1982); doi:10.1021/jm00350a016.
K. Kacprzak, Synlett, 943 (2005); doi:10.1055/s-2005-864809.
J. Finnerty and H. Wentrup, J. Org. Chem., 70, 9735 (2005); doi:10.1021/jo051389h.
H. Briehl, A. Lukosch and C. Wentrup, J. Org. Chem., 49, 2772 (1984); doi:10.1021/jo00189a025.
A.L. Barry, in ed: V.L. Corian, Procedure for Testing Antimicrobial Agents in Agar Media, Antibiotics in Laboratory Medicine, Williams and Wilkins, Baltimore, MD (1980).
K.D. Thomas, A.V. Adhikari and N.S. Shetty, Eur. J. Med. Chem., 45, 3803 (2010); doi:10.1016/j.ejmech.2010.05.030.