메뉴 건너뛰기




Volumn 44, Issue 8, 2014, Pages 1142-1148

Aluminium chloride-catalyzed synthesis of 4-benzyl cinnolines from aryl hydrazones

Author keywords

4 benzyl cinnolines; Aluminium chloride; Aryl hydrazones

Indexed keywords

4 BENZYL CINNOLINE DERIVATIVE; ALUMINUM CHLORIDE; CINNAMALDEHYDE; HETEROCYCLIC COMPOUND; HYDRAZONE DERIVATIVE; LEWIS ACID; TOLUENE; UNCLASSIFIED DRUG;

EID: 84897863300     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.853799     Document Type: Article
Times cited : (6)

References (24)
  • 1
    • 84867085510 scopus 로고    scopus 로고
    • Synthesis and pharmacological evaluation of pyrazolo[4,3-c]cinnoline derivatives as potential anti-inflammatory and antibacterial agents
    • 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.
    • (2012) Eur. J. Med. Chem. , vol.57 , pp. 176-184
    • Tonk, R.K.1    Bawa, S.2    Chawla, G.3    Deora, G.S.4    Kumar, S.5    Rathore, V.6    Mulakayala, N.7    Rajaram, A.8    Kalle, A.M.9    Afzal, O.10
  • 2
    • 0038626784 scopus 로고    scopus 로고
    • Structure and biological activity of some 4-amino-3-cinnolinecarboxylic acid derivatives: QSAR analysis of cinnoline derivatives with antibacterial properties
    • Brzezi ska, E.; Sta czak, 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.
    • (2003) Acta Pol. Pharm. , vol.60 , pp. 15-20
    • Brzezi Ska, E.1    Sta Czak, A.2    Ochocki, Z.3
  • 4
    • 0026769902 scopus 로고
    • Synthesis and antimicrobial and anti-inflammatory activities of substituted 2-mercapto-3-(N-aryl)pyrimido[5,4-c]cinnolin-4-(3H)-ones
    • 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.
    • (1992) J. Pharm. Sci. , vol.81 , pp. 365-366
    • Nargund, L.1    Badiger, V.2    Yarnal, S.3
  • 6
    • 0037375664 scopus 로고    scopus 로고
    • Substituted dibenzo[c,h] cinnolines: Topoisomerase I-targeting anticancer agents
    • 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.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 1475-1491
    • Yu, Y.1    Singh, S.K.2    Liu, A.3    Li, T.K.4    Liu, L.F.5    Lavoie, E.J.6
  • 8
    • 33645796232 scopus 로고    scopus 로고
    • 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
    • Lewgowd, W.; Sta czak, 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.
    • (2005) Acta Pol. Pharm. , vol.62 , pp. 105-110
    • Lewgowd, W.1    Sta Czak, A.2    Ochocki, Z.3    Krajewska, U.4    Rózalski, M.5
  • 9
    • 31544447715 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of new quinazoline and cinnoline derivatives as potential atypical antipsychotics
    • 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.
    • (2006) Chem. Biodivers. , vol.3 , pp. 106-117
    • Alvarado, M.1    Barceló, M.2    Carro, L.3    Masaguer, C.F.4    Ravina, E.5
  • 10
    • 82755194925 scopus 로고    scopus 로고
    • Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties
    • 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.
    • (2011) Polymer , vol.52 , pp. 6011-6019
    • Chen, J.-C.1    Wu, H.-C.2    Chiang, C.-J.3    Peng, L.-C.4    Chen, T.5    Xing, L.6    Liu, S.-W.7
  • 11
    • 1542602079 scopus 로고
    • New aspects of the electroreduction of azo compounds: Disproportionation reaction of the protonated radical anion ARNHNAR of benzo[c]cinnoline
    • 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.
    • (1988) J. Org. Chem. , vol.53 , pp. 5781-5783
    • Mugnier, Y.1    Laviron, E.2
  • 12
    • 0030152527 scopus 로고    scopus 로고
    • Electrochemical oxidation and structural changes of 5,6-dihydrobenzo[c] cinnolines
    • 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.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5020-5030
    • Dietrich, M.1    Heinze, J.2    Krieger, C.3    Neugebauer, F.A.4
  • 13
    • 33748251465 scopus 로고    scopus 로고
    • Synthesis and molluscicidal activity of new cinnoline and pyrano[2,3-c]pyrazole derivatives
    • 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.
    • (2006) Arch. Pharm. , vol.339 , pp. 456-446
    • Abdelrazek, F.M.1    Metz, P.2    Metwally, N.H.3    El-Mahrouky, S.F.4
  • 14
    • 0028227680 scopus 로고
    • A convenient synthesis of 4-chloro-and 4-bromocinnolines from o-aminophenylacetylenes
    • 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.
    • (1994) Synth. Commun. , vol.24 , pp. 1733-1736
    • Vasilevsky, S.F.1    Tretyakov, E.V.2    Verkruijsse, H.D.3
  • 15
    • 84897829958 scopus 로고
    • Base-catalyzed transformations of iminium phenylhydrazones: A new convenient synthesis of imidazo[1,2a]azacycloalkanes
    • 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.
    • (1981) Tetrahedron , vol.37 , pp. 1513-3518
    • Kanner, C.B.1    Pandit, U.K.2
  • 16
    • 0038106667 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2003) Tetrahedron , vol.59 , pp. 5919-5926
    • Tapolcsanyi, P.1    Maes, B.U.W.2    Monsieurs, K.3    Lemiere, G.L.F.4    Riedl, Z.5    Hajos, G.6    Driessche, B.V.7    Dommissea, R.A.8    Matyus, P.9
  • 17
    • 0005916711 scopus 로고
    • Cinnolines, IV: Synthesis of 3-acetyl-and 3-carbethoxycinnolines
    • Baumgarten, H. E.; Anderson, C. H. Cinnolines, IV: Synthesis of 3-acetyl-and 3-carbethoxycinnolines. J. Am. Chem. Soc. 1958, 80, 1981.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 1981
    • Baumgarten, H.E.1    Anderson, C.H.2
  • 18
    • 0037459870 scopus 로고    scopus 로고
    • An efficient and facile synthesis of substituted cinnoline and benzo[h] cinnoline derivatives
    • Gomma, M. A. M. An efficient and facile synthesis of substituted cinnoline and benzo[h] cinnoline derivatives. Tetrahedron Lett. 2003, 44, 3493.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3493
    • Gomma, M.A.M.1
  • 19
    • 0028952570 scopus 로고
    • Trifluoromethyl group in the synthesis of heterocyclic compounds: New and efficient synthesis of 3-aryl-4-aminocinnolines
    • 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.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1383-1386
    • Kiselyov, A.S.1
  • 20
    • 50149122391 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2008) J. Org. Chem. , vol.73 , pp. 6363-6368
    • Hasegawa, K.1    Kimura, N.2    Arai, S.3    Nishida, A.4
  • 21
    • 65549126243 scopus 로고    scopus 로고
    • Novel process to 4,4-dialkyl-1,4-dihydro-6-methoxy-3-phenylcinnolines via Grignard reaction
    • 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.
    • (2009) Heterocycles , vol.77 , pp. 273
    • Chen, D.1    Yang, C.2    Xie, Y.3    Ding, J.4
  • 22
    • 84864869808 scopus 로고    scopus 로고
    • Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines
    • 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.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8318-8321
    • Zhang, G.1    Miao, J.2    Zhao, Y.3    Ge, H.4
  • 23
    • 49149089645 scopus 로고    scopus 로고
    • 1-(4-nitrophenyl)-2-(3-phenylallylidene)hydrazine
    • Bao, F.-Y. 1-(4-Nitrophenyl)-2-(3-phenylallylidene)hydrazine. Acta Cryst. 2008, E64, 1531.
    • (2008) Acta Cryst , vol.E64 , pp. 1531
    • Bao, F.-Y.1
  • 24
    • 0005146930 scopus 로고
    • Cinnoline chemistry, I: Some condensation reactions of 4-chlorocinxolise
    • Castle, R. N.; Kruse, F. H. Cinnoline chemistry, I: Some condensation reactions of 4-chlorocinxolise. J. Org. Chem. 1952, 17, 1571-1575.
    • (1952) J. Org. Chem. , vol.17 , pp. 1571-1575
    • Castle, R.N.1    Kruse, F.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.