Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 12
848
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Iodine- and Indium(III) Chloride–Catalyzed Facile Syntheses of 1,5- and 1,8-Naphthyridines

&
Pages 1843-1851 | Received 05 Feb 2010, Published online: 29 Apr 2011

REFERENCES

  • (a) Bemis , G. W. ; Murcko , M. A. The properties of known drugs. 1. Molecular frameworks . J. Med. Chem. 1996 , 39 , 2887 – 2893 ; (b) Waterbeemd , H. ; Smith , D. A. ; Beaumont , K. ; Walker , D. K. Property-based design: Optimization of drug absorption and pharmacokinetics . J. Med. Chem. 2001 , 44 , 1313 – 1333 .
  • (a) Allott , C. P. ; Bradbury , R. H. ; Dennis , M. ; Fisher , E. ; Luke , R. W. A. ; Major , J. S. ; Oldham , A. A. ; Pearce , R. J. ; Reid , A. C. ; Roberts , D. A. ; Rudge , D. A. ; Russell , S. T. Quinoline, 1,5-naphthyridine and pyridine derivatives as potent, nonpeptidic angiotensin II receptor antagonists . Bioorg. Med. Chem. Lett. 1993 , 3 , 899 – 904 ; (b) Norman , M. H. ; Smith , H. D. ; Andrews , C. W. ; Tang , F. L. M. ; Cowan , C. L. ; Steffen , R. P. 4-(Heteroarylthio)-2-biphenylyltetrazoles as nonpeptide angiotensin II antagonists . J. Med. Chem. 1995 , 38 , 4670 – 4678 ; (c) Takeuchi , I. ; Hamada , Y. Syntheses of nitrogen-containing heterocyclic compounds, XXIII: Reaction of naphthyridine derivatives, with special reference to that of 1,7-naphthyridine . Chem. Pharm. Bull. 1976 , 24 , 1813 – 1821 ; (d) Bisagni , E. ; Landmass , C. ; Thirot , S. ; Huel , C. A convenient way to dibenzo[c,h]-1,5-naphthyridines (11-aza-benzo[c] phenanthridines) . Tetrahedron 1996 , 52 , 10427 – 10440 ; (e) Viti , G. ; Giannotti , D. ; Nannicini , R. ; Balacco , G. ; Pestellini , V. Synthesis of a benzo[b]-1,5-naphthyridine derivative as a potential constrained NK1 receptor antagonist . Tetrahedron Lett. 1994 , 35 ( 32 ), 5939 – 5942 .
  • Boros , E. E. ; Edwards , C. E. ; Foster , S. A. ; Fuji , M. ; Fujiwara , T. ; Garvey , E. P. ; Golden , P. L. ; Hazen , R. J. ; Jeffrey , J. L. ; Johns , B. A. ; Kawasuji , T. ; Kiyama , R. ; Koble , C. S. ; Kurose , N. ; Miller , W. H. ; Mote , A. L. ; Murai , H. ; Sato , A. ; Thompson , J. B. ; Woodward , M. C. ; Yoshinaga , T. Synthesis and antiviral activity of 7-benzyl-4-hydroxy-1,5-naphthyridin-2(1H)-one HIV integrase inhibitors . J. Med. Chem. 2009 , 52 , 2754 – 2761 .
  • (a) Gellibert , F. ; Woolven , J. ; Fouchet , M.-H. ; Mathews , N. ; Goodland , H. ; Lovegrove , V. ; Laroze , A. ; Nguyen , V.-L. ; Sautet , S. ; Wang , R. ; Janson , C. ; Smith , W. ; Krysa , G. ; Boullay , V. ; Gouville , A.-C. ; Huet , S. ; Hartley , D. Identification of 1,5-naphthyridine derivatives as a novel series of potent and selective TGF-β type I receptor inhibitors. J. Med. Chem. 2004, 47, 4494–4506; (b) Zhu , S. ; Zhang , Q. ; Gudise , C. ; Meng , L. ; Wei , L. ; Smith , E. ; Kong , Y. Synthesis and evaluation of naphthyridine compounds as antimalarial agents. Bioorg. Med. Chem. Lett. 2007, 17, 6101–6106; (c) Roma , G. ; Grossi , G. ; Di Braccio , M. ; Piras , D. ; Ballabeni , V. ; Tognolini , M. ; Bertoni , S. ; Barocelli , E. 1,8-Naphthyridines, VII: New substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides and their isosteric analogues, exhibiting notable anti-inflammatory and/or analgesic activities, but no acute gastrolesivity. Eur. J. Med. Chem. 2008, 43, 1665–1680; (d) Ghosh , K. ; Sena , T. ; Frohlich , R. A naphthyridine-based receptor for sensing citric acid. Tetrahedron Lett. 2007, 48, 2935–2938; (e) Mogilaiah , K. ; Vidya , K. ; Kavitha , S. ; Kumar , K. S. A naphthyridine-based receptor for sensing citric acid. Indian J. Chem. 2009, 48B, 282–285; (f) Feng , W. ; Satyanarayana , M. ; Cheng , L. ; Liu , A. ; Tsai , Y-C. ; Liu , L. F. ; LaVoie , E. J. Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]-naphthyridines as novel topoisomerase I-targeting antitumor agents. Bioorg. Med. Chem. 2008, 16, 9295–9301; (g) Fine , S. A. ; Heindel , N. D. Synthesis and antimalarial activity of 4-aminobenzo[b]-l,5-naphthyridine. J. Med. Chem. 1970, 13, 760–762.
  • (a) Zhu , S. ; Moreno , K. X. ; Jenkins , R. M. ; Walmsley , J. A. Interactions of 1,5-naphthyridine with Pd(en)Cl2 or [Pd(en)(H2O)2](NO3)2 in aqueous solution . Dalton Trans. 2008 , 6401 – 6408 ; (b) Singh , A. N. ; Thummel , R. P. 1,5-Naphthyridine as a new linker for the construction of bridging ligands and their corresponding Ru(II) complexes . Inorg. Chem. 2009 , 48 , 6459 – 6408 ; (c) Kimura , M. ; Tanaka , K. Synthesis and electrochemical reduction of a ruthenium complex bearing an N,N-bis[(benzo[g][1,5]naphthyridin-2-yl)methyl]propane-2-amine ligand as an NAD+/NADH-type redox site . Angew. Chem. Int. Ed. 2008 , 47 , 9768 – 9771 .
  • Liao , S.-H. ; Shiu , J.-R. ; Liu , S.-W. ; Yeh , S.-J. ; Chen , Y.-H. ; Chen , C.-T. ; Chow , T. J. ; Wu , C.-I. Hydroxynaphthyridine-derived group III metal chelates: Wide band gap and deep blue analogues of green Alq3 (tris(8-hydroxyquinolate)aluminum) and their versatile applications for organic light-emitting diodes . J. Am. Chem. Soc. 2009 , 131 , 763 – 777 .
  • Adimurthy , S. ; Malakar , C. C. ; Beifuss , U. The influence of bases and ligands on the outcome of the Cu(I)-catalyzed oxidative homocoupling of terminal alkynes to 1,4-disubstituted 1,3-diynes using oxygen as an oxidant . J. Org. Chem. 2009 , 74 , 5648 – 5651 .
  • (a) Hauser , C. R. ; Reynolds , G. A. Relative ease of cyclization of 2-, 3-, and 4-aminopyridine derivatives: Synthesis of naphthyridines . J. Org. Chem. 1950 , 15 , 1224 – 1232 ; (b) Hart , E. P. Naphthyridines, Part I: The chemistry of 1,5-naphthyridine . J. Chem. Soc. , 1954 , 1879 – 1882 ; (c) Albert , A. Naphthyridines: Ionization constants and hpectra of four parent substances . J. Chem. Soc. 1960 , 1790 – 1793 ; (d) Rapoyort , H. ; Batcho , A. D. 1,5-Naphthyridine and some of its alkyl derivatives . J. Org. Chem. 1963 , 28 , 1753 – 1759 ; (e) Paudler , W. W. ; Kress , T. J. Ten π-electron nitrogen heterocyclic compounds, IX: The syntheses and nuclear magnetic resonance spectra of some methylnaphthyridines . J. Org. Chem. 1966 , 31 , 3055 – 3057 ; (f) Paudler , W. W. ; Kress , T. J. Naphthyridine chemistry, V: One-step synthesis of 1,8-naphthyridines . J. Org. Chem. 1967 , 32 , 832 – 833 ; (g) Armarego , W. L. F. Naphthyridines, part-III: Tetrahydro- and decahydro-l,5-,-1.6-, -1.7-, and -1.8-naphthyridines . J. Chem. Soc. 1967 , 377 – 383 ; (h) Hamada , Y. ; Takeuchi , I. Synthesis of nitrogen containing compounds, XVIII: Synthesis of naphthyridine by improved one step process . Chem. Pharm. Bull. 1971 , 19 , 1857 – 1862 .
  • (a) Santos , A. G. O. ; Klute , W. ; Torode , J. ; Bohm , V. P. W. ; Cabrita , E. ; Runsink , J. ; Hoffmann , R. W. Flexible molecules with defined shape, X: Synthesis and conformational study of 1,5-diaza-cis-decalin . New J. Chem. 1998 , 993 – 997 ; (b) Li , X. ; Schenkel , L. B. ; Kozlowski , M. C. Synthesis and resolution of a novel chiral diamine ligand and application to asymmetric lithiation−substitution . Org. Lett. 2000 , 2 , 875 – 878 .
  • Unlike quinoline synthesis by catalytic methods [(a) Sridharan , V. ; Ribelles , P. ; Ramos , M. T. ; Menendez , J. C. Cerium(IV) ammonium nitrate is an excellent, general catalyst for the Friedlander and Friedlander–Borsche quinoline syntheses: Very efficient access to the antitumor alkaloid luotonin A. J. Org. Chem. 2009, 74, 5715–5718; (b) Zhang , X. L. ; Wang , Q. Y. ; Sheng , S. R. ; Wang , Q. ; Liu , X. L. Efficient Friedländer synthesis of quinoline derivatives from 2-aminoarylketones and carbonyl compounds mediated by recyclable PEG-supported sulfonic acid. Synth. Commun. 2009, 39, 3293–3304, ] naphthyridine synthesis is not explored.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.