SYNTHESIS OF ISOMERIC NAPHTHYRIDINES
1451
3. Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, M. 1,8-Naphthyridines IV:
9-Substituted N,N-dialkyl-5-(alkylamino or cycloalkylamino)[1,2,4]triazolo[4,3-a][1,8]
naphthyridine-6-carboxamides: New compounds with anti-aggressive and potent anti-
inflammatory activities. Eur. J. Med. Chem. 2000, 35, 1021.
4. (a) Larsen, R. D.; Corley, E. G.; King, A. O.; Carrol, J. D.; Davis, P.; Verhoeven, T. R.;
Reider, P. J.; Labelle, M.; Gauthier, J. Y.; Xiang, Y. B.; Zamboni, R. J. Practical route to
a new class of LTD4 receptor antagonists. J. Org. Chem. 1996, 61, 3398; (b) Maguire,
M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. A new series of PDGF
receptor tyrosine kinase inhibitors: 3-Substituted quinoline derivatives. J. Med. Chem.
1994, 37, 2129.
5. (a) Mahata, P. K.; Venkatesh, C.; Syam Kumar, U. K.; Ila, H.; Junjappa, H. Reaction of
r-oxoketene-N,S-arylaminoacetals with Vilsmeier reagents: An efficient route to highly
functionalized quinolines and their benzo=hetero-fused analogues. J. Org. Chem. 2003,
68, 3966; (b) Tokuyama, H.; Sato, M.; Ueda, T.; Fukuyama, T. A practical route to
quinolines from anilines. Heterocycles 2001, 54, 105.
6. Jones, G. In Comprehensive Heterocyclic Chemistry II; A. R. Katritzky, C. W. Rees, and
E. F. V. Scriven (Eds.); Pergamon Press: Oxford, 1996; vol. 5, Chapter 5.05, p. 167.
7. (a) Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T. J.; Shim, S. C. Synthesis of quinolines via
ruthenium-catalysed amine exchange reaction between anilines and trialkylamines. Chem.
Commun. 2000, 1885; (b) Tom, N. J.; Ruel, E. M. An efficient synthesis of substituted
quinolines. Synthesis 2001, 1351; (c) Matsugi, M.; Tabusa, F.; Minamikawa, J. Doebner–
Miller synthesis in a two-phase system: Practical preparation of quinolines. Tetrahedron
Lett. 2000, 41, 8523; (d) Ranu, B. C.; Hajra, A.; Jana, U. Efficient microwave-assisted
synthesis of quinolines and dihydroquinolines under solvent-free conditions. Tetrahedron
Lett. 2000, 41, 531.
8. (a) Campos, P. J.; Anon, E.; Malo, M. C.; Tan, C.-Q.; Rodriguez, M. A. Synthesis of
substituted benzoquinolines by the irradiation of 3-amino-2-alkene imines. Tetrahedron
1998, 54, 6929; (b) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Intramolecular radical
additions to quinolines. Tetrahedron Lett. 2001, 42, 2907.
9. (a) Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Highly regio-
selective Friedlander reaction. Org. Lett. 2001, 3, 1101; (b) Wrobel, Z. Transformation
of 2,2-dioxoisothiazolo[5,4,3-d,e]quinolines to pyrrolo[4,3,2-d,e]quinolin-2(1H)-ones.
Tetrahedron Lett. 2001, 42, 5537.
10. (a) Charmantray, F.; Demeunynck, M.; Lhomme, J.; Duflos, A. J. New route to extended
angular polyaza-heterocycles. J. Org. Chem. 2001, 66, 8222; (b) Demeunynck, M.;
Moucheron, C.; Mesmaeker, A. K. D. Tetrapyrido[3,2-a:20,30-c:300,200-h:2000,3000-j]acridine
(tpac): A new extended polycyclic bis-phenanthroline ligand. Tetrahedron Lett. 2002, 43, 261.
11. Peng, B. H.; Liu, G. F.; Liu, L.; Jia, D. Z. Studies on solid-state proton transfer along
hydrogen bond of pyrazolone ring. Tetrahedron 2005, 61(24), 5926.
12. Garnovskii, A. D.; Vasilchenko, I. S. Tautomerism and various coordination modes of
typical chelating ligands with metals. Usp. Khim. 2005, 74(3), 211.
13. Raczynska, E. D.; Kosinska, W.; Osmialowski, B.; Gawinecki, R. Tautomeric equilibria
in relation to pi-electron delocalization. Chem. Rev. 2005, 105(10), 3561.
14. Ljunggren, B.; Wirestrand, L. E. Phototoxic properties of quinine and quinidine: Two
quinoline methanol isomers. Photodermatol. 1988, 5(3), 133.
15. Lanfranchia, D. A.; Vellutinia, M.; Blanca, M. C.; Bradesia, P.; Casanovaa, J.; Tomi, F.
Enantiomeric differentiation of oxygenated bicyclo[2.2.1]heptane derivatives by 13C NMR
spectroscopy using Yb(hfc)3. Spectrosc. Lett. 2010, 43, 36.
16. Giorgi, G.; Salvini, L.; Ponticelli, F. Gas phase ion chemistry of the heterocyclic isomers
3-methyl-1,2-benzisoxazole and 2-methyl-1,3-benzoxazole. J. Am. Soc. Mass Spectr. 2004,
15, 1005.