Facile Synthesis of 1-Hydroxy-5-methoxy-Benzo[f][2,7]naphthyridines

REFERENCES

• Joseph , P. M. Quinoline, quinazoline, and acridone alkaloids . Nat. Prod. Rep. 2004 , 650 – 668 ; Nat. Prod. Rep. 2003, 476–493 .
   Google Scholar
• Alhaider , A. A. ; Abdelkader , M. A. ; Lien , E. J. Conformationally defined adrenergic agents, 1: Design and synthesis of novel α 2 selective adrenergic agents: Electrostatic repulsion–based conformational prototypes . J. Med. Chem. 1985 , 28 ( 10 ), 1398 – 1404 .
   PubMed Web of Science ®Google Scholar
• Campbell , S. F. ; Hardstone , J. D. ; Palmer , M. J. 2,4-Diamino-6,7-dimethoxyquinoline derivatives as cui-adrenoceptor antagonists and antihypertensive agents . J. Med. Chem. 1988 , 31 ( 5 ), 1031 – 1035 .
   PubMed Web of Science ®Google Scholar
• Wu , D. Towards new anticancer drugs: A decade of advances in synthesis of capmptothecin and related alkaloids . Tetrahedron 2003 , 59 ( 44 ), 8649 – 8687 .
   Web of Science ®Google Scholar
• Meth-Cohn , O. The synthesis of pyridines, quinolines, and other related systems by the Vilsmeier and the reverse Vilsmeier method . Heterocycles 1993 , 35 , 539 – 557 .
   Web of Science ®Google Scholar
• Bracher , F. Polycyclic aromatic alkaloids, 10: Annonaceous alkaloids with antimycotic activity . Arch. Pharm. Weinheim. 1994 , 327 , 371 – 375 .
   Google Scholar
• Tadeusz , F. M. Marine pyridoacridine alkaloids: Structure, synthesis, and biological chemistry . Chem. Rev. 1999 , 93 , 1825 – 1838 .
   Google Scholar
• Peterson , R. J. ; Zjawiony , J. K. ; Liu , S. ; Hufford , C. D. ; Clark , A. M. ; Rogers , R. D. Copyrine alkaloids: Synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines . J. Med. Chem. 1992 , 35 ( 22 ), 4069 – 4077 .
   PubMed Web of Science ®Google Scholar
• Gorlitzer , K. ; Bode , M. ; Jones , P. G. ; Jomaa , H. ; Wiesner , J. Benzo[c][2,7]naphthyridine-5-yl-amines and benzo[h][2,7]naphthyridine-5-yl-amines: Potential antimalarials . Pharmazie 2007 , 62 ( 1 ), 15 – 26 .
   PubMed Web of Science ®Google Scholar
• Bonard , I. ; Bontemps , N. ; Lamphy , S. ; Banaigs , B. ; Coloson , P. ; Hossier , C. ; Waring , M. J. ; Bailly , C. Binding to DNA and cytotoxic evaluation of ascididemins, the major alkaloid from the Mediterranean Ascidian cystodytes dellechiajei . Anti-Cancer Drug Des. 1995 , 10 ( 4 ), 333 – 346 .
   PubMedGoogle Scholar
• Meth-Cohn , O. ; Narine , B. A versatile new synthesis of quinolines and related fused pyridines, part 1 . Tetrahedron Lett. 1978 , 19 , 2045 .
   Google Scholar
• Meth-Cohn , O. ; Narine , B. ; Tarnowski , B. A versatile new synthesis of quinolines and related fused pyridines, part 5: The synthesis of 2-chloroquinoline-3-aldehydes . J. Chem. Soc. Perkin Trans. 1 1981 , 1520 .
   Google Scholar
• Arulprakash , G. ; Sampathkumar , N. ; Rajendran , S. P. Synthesis of cyclopenta[b]benzo[g][1,8]naphthyridines . Asian J. Chem. 2002 , 14 , 1303 – 1306 .
   Google Scholar
• Meth-Cohn , O. ; Narine , B. ; Tarnowski , B. A versatile new synthesis of quinolines and related fused pyridines, part 9: Applications of 2-chloroquinoline-3-aldehydes . J. Chem. Soc., Perkin Trans. 1 1981 , 509 – 2517 .
   Google Scholar
• Miklos , N. ; Aron , P. ; Andrea , V. ; Gabor , B. ; Laszlo , T. Synthesis of pyrrolo[3,4-c] quinolines by 1,5-electrocyclisation of non-stabilised azomethine ylides . Tetrahedron 2005 , 61 , 8199 – 8205 .
   Google Scholar
• Sartori , S. ; Ballini , R. ; Bigi , F. ; Bosica , G. ; Maggi , R. ; Righi , P. Protection (and deprotection) of functional groups in organic synthesis by heterogeneous catalysis. Chem. Rev. 2004, 104, 199–250.
   PubMed Web of Science ®Google Scholar
• Timea , B. ; Arpad , M. Microwave-assisted acetalization of carbonyl compounds catalyzed by reusable “envirocat” supported reagents . Synth. Commun. 1997 , 27 ( 21 ), 3705 – 3709 .
   Web of Science ®Google Scholar
• Kerry , M. A. ; Boyd , G. W. ; Mackay , S. P. ; Meth-Cohn , O. ; Platt , L. The synthesis of benzo[h]quinolines as topoisomerase inhibitors . J. Chem. Soc., Perkin Trans. 1 1999 , 2315 – 2321 .
   Google Scholar
• Leonard , N. J. ; Herbrandson , H. F. ; Van Heyningen , E. M. Synthesis of 4 hydroxy quinolines, VI: Synthesis of 3-n-heptyl-7-methoxy-2-methyl-4-quinolinol . J. Am. Chem. Soc. 1946 , 68 ( 7 ), 1279 – 1281 .
   PubMedGoogle Scholar
• Testaferri , L. ; Tiecco , M. ; Tingoli , M. ; Chianelli , D. ; Montanucci , M. The reactions of unactivated aryl halides with sodium methoxide in HMPA: Synthesis of phenols, anisoles, and methoxy phenols . Tetrahedron 1983 , 39 , 193 – 197 .
   Google Scholar
• Sampathkumar , N. ; Rajendran , S. P. Functionalization of quinolines: Preparation of 2-formyl-4-methoxy quinolines . Asian J. Chem. 2004 , 16 ( 3–4 ), 1931 – 1933 .
   Google Scholar
• Hoyle , W. ; Roberts , G. P. ; Meth-Cohn , O. Potential antimicrobial furans . J. Med. Chem. 1973 , 16 ( 6 ), 709 – 710 .
   PubMedGoogle Scholar
• Sampathkumar , N. ; Ramalingam , S. T. ; Rajendran , S. P. A. Facile synthesis of 1-hydroxy-5-chloro-benzo[f][2,7]naphthyridines . Indian J. Chem. 2005 , 44B , 2608 – 2610 .
   Google Scholar
• 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 .
   Google Scholar