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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 10
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Original Articles

Synthesis and Spectroscopic Distinction of Benzonaphthonaphthyridine and Its Isomer

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Pages 1441-1452 | Received 30 Apr 2013, Published online: 29 Apr 2014

REFERENCES

  • (a) Michael , J. P. Quinoline, quinazoline, and acridone alkaloids . Nat. Prod. Rep. 1997 , 14 , 605 ; (b) Comprehensive Heterocyclic Chemistry II; A. R. Katritzky, C. W. Rees, E. F. V. Scriven (Eds.); Pergamon Press: Oxford, New York, 1996; vol. 5, p. 245.
  • Chen , Y. L. ; Fang , K. C. ; Sheu , J. Y. ; Hsu , S. L. ; Tzeng , C. C. Synthesis and antibacterial evaluation of certain quinolone derivatives . J. Med. Chem. 2001 , 44 , 2374 .
  • 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.
  • (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 .
  • (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 .
  • 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 .
  • (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 .
  • (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 .
  • (a) Hsiao , Y. ; Rivera , N. R. ; Yasuda , N. ; Hughes , D. L. ; Reider , P. J. Highly regioselective 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 .
  • (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:2′,3′-c:3″,2″-h:2′″,3′″-j]acridine (tpac): A new extended polycyclic bis-phenanthroline ligand . Tetrahedron Lett. 2002 , 43 , 261 .
  • 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 .
  • Garnovskii , A. D. ; Vasilchenko , I. S. Tautomerism and various coordination modes of typical chelating ligands with metals . Usp. Khim. 2005 , 74 ( 3 ), 211 .
  • Raczynska , E. D. ; Kosinska , W. ; Osmialowski , B. ; Gawinecki , R. Tautomeric equilibria in relation to pi-electron delocalization . Chem. Rev. 2005 , 105 ( 10 ), 3561 .
  • Ljunggren , B. ; Wirestrand , L. E. Phototoxic properties of quinine and quinidine: Two quinoline methanol isomers . Photodermatol. 1988 , 5 ( 3 ), 133 .
  • 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 .
  • 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 .
  • Zheng-Guo , H. ; Chun-Bao , M. ; Shi , F. Diversity synthesis of N-substituted 2-amino-1,6-naphthyridine derivatives under microwave irradiation. J. Comb. Chem. 2010, 12, 16.
  • Ghotekar , B. K. ; Ghagare , M. G. ; Toche , R. B. ; Jachak , M. N. Synthesis of new quinoline fused heterocycles such as benzo[h]-1,6-naphthyridines and pyrazolo[4,3-c]quinolines . Monatsh. Chem. 2010 , 141 , 169 .
  • Xiang-Shan , W. ; Qing , L. ; Jian-Rong , W. ; Chang-Sheng , Y. ; Shu-Jiang , T. A. Novel and efficient method for the synthesis of 5-arylnaphtho[2,1-c][2,7]naphthyridine derivatives catalyzed by iodine . J. Heterocycl. Chem. 2009 , 46 , 1229 .
  • Xiang-Shan , W. ; Qing , L. ; Jian-Rong , W. ; Shu-Jiang , T. Efficient method for the synthesis of pyranoquinoline, thiopyranoquinoline, thienoquinoline, and naphtho[2,7]naphthyridine derivatives catalyzed by iodine . J. Comb. Chem. 2009 , 11 , 433 .
  • Prabha , K. ; Rajendra Prasad , K. J. Dinaphthonaphthyridines: A class of novel molecules with potent antioxidant and anticancer agents . Med. Chem. Commun. 2013 , 4 , 340 .
  • Prabha , K. ; Rajendra Prasad , K. J. Synthesis of alkyl and aryl substituted benzo[h]naphtho[1,2-b]naphthyridines . Synth. Commun. 2012 , 42 , 2277 .

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