A one-pot synthesis of 9-chloro-6-methyl-7-phenyldibenzo[b,h][1,6]naphthyridines from 4-chloro-2-methylquinolines is reported. Since the yield of the dibenzonaphthyridine was low, in an alternative method the title compounds were prepared from the 4-chloro-2-methylquinolines via 2-methyl-4-[(4-chlorophenyl)amino]quinolines as intermediates, which provided improved yields.
CurdF.H. S., RaisonC. G., and RoseF. L., J. Chem. Soc., 1947, 898.
2.
EmbreyM.W., WaiJ. S., FunkT. W., HomnickC. F., PerlowD. S., YoungS. D., VaccaJ. P., HazudaD. J., FelockP. J., StillmockK. A., WitmerM. V., MoyerG., SchleifW. A., GabryelskiL. J., JinL., ChenI. W., EllisJ. D, WongB. K., LinJ. H., LeonardY. M., TsouN. N., and ZhuangL., Bioorg. Med. Chem. Lett., 2005, 15, 4550.
3.
ZhuangL., WaiJ. S., EmbreyM. W., FisherT. E., EgbertsonM. S., PayneL. S., GuareJ. P., VaccaJ. P., HazudaD. J., FelockP. J., WolfeA. L., StillmockK. A., WitmerM. V., MoyerG., SchleifW. A., GabryelskiL. J., LeonardY. M., LynchJ. J., MichelsonS. R., and YoungS. D., J. Med. Chem., 2003, 46, 453.
4.
AtanasovaM., IlievaS., and GalabovB., Eur. J. Med. Chem., 2007. 42, 1184.
5.
GopalsamyA., ShiM., BoschelliD. H., WilliamsonR., OllandA., HuY., KrishnamurthyG., HanX., ArndtK., and GuoB., J. Med. Chem., 2007. 50, 5547.
6.
PriceC.C., MaynertE. W., and BoekelheideV., J. Org. Chem., 1949, 14, 484.
7.
RossiterS., PeronJ. M., WhitfieldP. J., and JonesK., Bioorg. Med. Chem. Lett., 2005, 15, 4806.
8.
SekarM., and Rajendra PrasadK. J., Indian J. Chem., 1999, 38B, 969.
9.
GopalasamyA., ShiM., and NilakantanR., Org. Process Res. Dev., 2005. 11, 450.
10.
LeslieD., ThomasR., LiZ., BruceB. C., and WilliamsD. A., J. Med. Chem., 2003, 46, 1049.
11.
MackayS.P., and Meth-CohnO., Synthesis, 2000, 1121.
12.
Da SettimoA., BiajiG., PrimfioreG., FerrariniP. L., LiviO., and MariniA. M., J. Het. Chem., 1980, 17, 1225.
13.
KidwaiM., and KohliS., Indian J. Chem., 2001, 40B, 248.
14.
SridharanM., and Rajendra PrasadK. J., J. Chem. Res., 2007, 164.
