Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones

REFERENCES

• Tonk , R. K ; Bawa , S. ; Chawla , G. ; Deora , G. S. ; Kumar , S. ; Rathore , V. ; Mulakayala , N. ; Rajaram , A. ; Kalle , A. M. ; Afzal , O. Synthesis and pharmacological evaluation of pyrazolo[4,3-c]cinnoline derivatives as potential anti-inflammatory and antibacterial agents . Eur. J. Med. Chem. 2012 , 57 , 176 – 184 .
   PubMed Web of Science ®Google Scholar
• Brzeziska , E. ; Staczak , A. ; Ochocki , Z. Structure and biological activity of some 4-amino-3-cinnolinecarboxylic acid derivatives: QSAR analysis of cinnoline derivatives with antibacterial properties . Acta Pol. Pharm. 2003 , 60 , 15 – 20 .
   PubMedGoogle Scholar
• Hennequin , L. F. ; Thomas , A. P. ; Johnstone , C. ; Stokes , E. S. ; Ple , P. A. ; Lohman , J.-J. ; Oqilve , D. J. ; Dukes , M. ; Wedge , S. R. ; Curwen , J. O. Design and structure–activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors . J. Med. Chem. 1999 , 42 , 5369 – 5389 .
   PubMed Web of Science ®Google Scholar
• Nargund , L. ; Badiger , V. ; Yarnal , S. Synthesis and antimicrobial and anti-inflammatory activities of substituted 2-mercapto-3-(N-aryl)pyrimido[5,4-c]cinnolin-4-(3H)-ones . J. Pharm. Sci. 1992 , 81 , 365 – 366 .
   PubMed Web of Science ®Google Scholar
• Bantick , J. ; Hirst , S. ; Perry , M. ; Phillips , E. Chem. Abstr. 1998 , 128 , 217375 .
   Google Scholar
• Yu , Y. ; Singh , S. K. ; Liu , A. ; Li , T. K. ; Liu , L. F. ; LaVoie , E. J. Substituted dibenzo[c,h]cinnolines: Topoisomerase I-targeting anticancer agents Bioorg . Med. Chem. 2003 , 11 , 1475 – 1491 .
   Web of Science ®Google Scholar
• Hu , E. ; Kunz , R. K. ; Rumfelt , S. ; Chen , N. ; Bürli , R. ; Li , C. ; Andrews , K. L. ; Zhang , J. ; Chmait , S. ; Kogan , J. ; Lindstrom , M. ; Hitchcock , S. A. ; Treanor , J. Bioorg. Med. Chem. Lett. 2012 , 22 , 2262 – 2265
   PubMed Web of Science ®Google Scholar
• Lewgowd , W. ; Staczak , A. ; Ochocki , Z. ; Krajewska , U. ; Rózalski , M. Synthesis and cytotoxicity of new potential intercalators based on tricyclic systems of some pyrimido[5,4-c]cinnoline and pyrimido[5,4-c]quinoline derivatives, part I . Acta Pol. Pharm. 2005 , 62 , 105 – 110 .
   PubMedGoogle Scholar
• Alvarado , M. ; Barceló , M. ; Carro , L. ; Masaguer , C. F. ; Ravina , E. Synthesis and biological evaluation of new quinazoline and cinnoline derivatives as potential atypical antipsychotics . Chem. Biodivers. 2006 , 3 , 106 – 117 .
   PubMed Web of Science ®Google Scholar
• Chen , J.-C. ; Wu , H.-C. ; Chiang , C.-J. ; Peng , L.-C. ; Chen , T. ; Xing , L. ; Liu , S.-W. Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties . Polymer 2011 , 52 , 6011 – 6019 .
   Web of Science ®Google Scholar
• Mugnier , Y. ; Laviron , E. New aspects of the electroreduction of azo compounds: Disproportionation reaction of the protonated radical anion ARNHNAR of benzo[c]cinnoline . J. Org. Chem. 1988 , 53 , 5781 – 5783 .
   Web of Science ®Google Scholar
• Dietrich , M. ; Heinze , J. ; Krieger , C. ; Neugebauer , F. A. Electrochemical oxidation and structural changes of 5,6-dihydrobenzo[c]cinnolines J. Am. Chem. Soc. 1996, 118, 5020–5030.
   Web of Science ®Google Scholar
• Abdelrazek , F. M. ; Metz , P. ; Metwally , N. H. ; El-Mahrouky , S. F. Synthesis and molluscicidal activity of new cinnoline and pyrano[2,3-c]pyrazole derivatives . Arch. Pharm. 2006 , 339 , 456 – 446 .
   PubMed Web of Science ®Google Scholar
• Vasilevsky , S. F. ; Tretyakov , E. V. ; Verkruijsse , H. D. A convenient synthesis of 4-chloro- and 4-bromocinnolines from o-aminophenylacetylenes . Synth. Commun. 1994 , 24 , 1733 – 1736
   Web of Science ®Google Scholar
• Kanner , C. B. ; Pandit , U. K. Base-catalyzed transformations of iminium phenylhydrazones: A new convenient synthesis of imidazo[1,2a]azacycloalkanes . Tetrahedron 1981 , 37 , 1513 – 3518 .
   Web of Science ®Google Scholar
• Tapolcsanyi , P. ; Maes , B. U. W. ; Monsieurs , K. ; Lemiere , G. L. F ; Riedl , Z. ; Hajos , G. ; Driessche , B. V. ; Dommissea , R. A. ; Matyus , P. Synthesis of the dibenzo[f,h]phthalazine and dibenzo[f,h]cinnoline skeleton via a “Suzuki–Pd-catalyzed intramolecular arylation” and a “Suzuki–Pschorr” approach . Tetrahedron , 2003 , 59 , 5919 – 5926 .
   Web of Science ®Google Scholar
• Baumgarten , H. E. ; Anderson , C. H. Cinnolines, IV: Synthesis of 3-acetyl- and 3-carbethoxycinnolines . J. Am. Chem. Soc. 1958 , 80 , 1981 .
   Web of Science ®Google Scholar
• Gomma , M. A. M. An efficient and facile synthesis of substituted cinnoline and benzo[h]cinnoline derivatives . Tetrahedron Lett. 2003 , 44 , 3493 .
   Web of Science ®Google Scholar
• Kiselyov , A. S. Trifluoromethyl group in the synthesis of heterocyclic compounds: New and efficient synthesis of 3-aryl-4-aminocinnolines . Tetrahedron Lett. 1995 , 36 , 1383 – 1386 .
   Web of Science ®Google Scholar
• Hasegawa , K. ; Kimura , N. ; Arai , S. ; Nishida , A. Novel synthesis of cinnolines and 1-aminoindolines via Cu-catalyzed intramolecular N-arylation of hydrazines and hydrazones prepared from 3-haloaryl-3-hydroxy-2-diazopropanoates . J. Org. Chem. 2008 , 73 , 6363 – 6368 .
   PubMed Web of Science ®Google Scholar
• Chen , D. ; Yang , C. ; Xie , Y. ; Ding , J. Novel process to 4,4-dialkyl-1,4-dihydro-6-methoxy-3-phenylcinnolines via Grignard reaction . Heterocycles 2009 , 77 , 273 .
   Web of Science ®Google Scholar
• Zhang , G. ; Miao , J. ; Zhao , Y. ; Ge , H. Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines . Angew. Chem. Int. Ed. 2012 , 51 , 8318 – 8321 .
   PubMed Web of Science ®Google Scholar
• Bao , F.-Y. 1-(4-Nitrophenyl)-2-(3-phenylallylidene)hydrazine . Acta Cryst. 2008 , E64 , 1531
   Google Scholar
• Castle , R. N. ; Kruse , F. H. Cinnoline chemistry, I: Some condensation reactions of 4-chlorocinxolise . J. Org. Chem. 1952 , 17 , 1571 – 1575 .
   Web of Science ®Google Scholar