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Volumn 13, Issue 5, 2011, Pages 466-477

Application of sequential Cu(I)/Pd(0)-catalysis to solution-phase parallel synthesis of combinatorial libraries of dihydroindeno[1,2-c]isoquinolines

Author keywords

combinatorial libraries of heterocycles; dihydroindenoisquinolines; multicomponent reactions; Solution phase parallel synthesis; transition metal catalyzed reactions

Indexed keywords

COPPER; INDENE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PALLADIUM;

EID: 80052752195     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200027c     Document Type: Article
Times cited : (8)

References (32)
  • 2
    • 74049128683 scopus 로고    scopus 로고
    • Solution-Phase Parallel Synthesis of Novel Membrane-Targeted Antibiotics
    • Vooturi, S. K.; Firestine, S. M. Solution-Phase Parallel Synthesis of Novel Membrane-Targeted Antibiotics J. Comb. Chem. 2010, 12, 151
    • (2010) J. Comb. Chem. , vol.12 , pp. 151
    • Vooturi, S.K.1    Firestine, S.M.2
  • 3
    • 64949196018 scopus 로고    scopus 로고
    • Solution-Phase Parallel Synthesis of Novel Spirooxazolinoisoxazolines
    • Shih, H.-W.; Guo, C.-W.; Lo, K.-H.; Huang, M.-Y.; Cheng, W.-C. Solution-Phase Parallel Synthesis of Novel Spirooxazolinoisoxazolines J. Comb. Chem. 2009, 11, 281
    • (2009) J. Comb. Chem. , vol.11 , pp. 281
    • Shih, H.-W.1    Guo, C.-W.2    Lo, K.-H.3    Huang, M.-Y.4    Cheng, W.-C.5
  • 6
    • 77953745157 scopus 로고    scopus 로고
    • Streamlining organic free radical synthesis through modern molecular technology: From polymer supported synthesis to microreactors and beyond
    • Zhang, S.; Chen, J.; Lykakis, I. N.; Perchyonok, V. R. Streamlining organic free radical synthesis through modern molecular technology: from polymer supported synthesis to microreactors and beyond Curr. Org. Synth. 2010, 7, 177
    • (2010) Curr. Org. Synth. , vol.7 , pp. 177
    • Zhang, S.1    Chen, J.2    Lykakis, I.N.3    Perchyonok, V.R.4
  • 7
    • 33644643208 scopus 로고    scopus 로고
    • Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides
    • Evindar, G.; Batey, R. A. Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides J. Org. Chem. 2006, 71, 1802
    • (2006) J. Org. Chem. , vol.71 , pp. 1802
    • Evindar, G.1    Batey, R.A.2
  • 8
    • 0141683733 scopus 로고    scopus 로고
    • Parallel Solution-Phase Asymmetric Synthesis of α-Branched Amines
    • Mukade, T.; Dragoli, D. R.; Ellman, J. A. Parallel Solution-Phase Asymmetric Synthesis of α-Branched Amines J. Comb. Chem. 2003, 5, 590
    • (2003) J. Comb. Chem. , vol.5 , pp. 590
    • Mukade, T.1    Dragoli, D.R.2    Ellman, J.A.3
  • 9
  • 10
    • 77949381877 scopus 로고    scopus 로고
    • Synthesis of 1-(1 H -Indol-3-yl)-1,2-dihydroisoquinolines via AgOTf-Catalyzed Three-Component Reactions of 2-Alkynylbenzaldehydes, Amines, and Indoles
    • Yu, X.; Wu, J. Synthesis of 1-(1 H -Indol-3-yl)-1,2-dihydroisoquinolines via AgOTf-Catalyzed Three-Component Reactions of 2-Alkynylbenzaldehydes, Amines, and Indoles J. Comb. Chem. 2010, 12, 238
    • (2010) J. Comb. Chem. , vol.12 , pp. 238
    • Yu, X.1    Wu, J.2
  • 11
    • 78149311873 scopus 로고    scopus 로고
    • Three-Component One-Pot Approach to Synthesize Benzopyrano[4,3- d ]pyrimidines
    • Li, D.; Duan, S.; Hu, Y. Three-Component One-Pot Approach to Synthesize Benzopyrano[4,3- d ]pyrimidines J. Comb. Chem. 2010, 12, 895
    • (2010) J. Comb. Chem. , vol.12 , pp. 895
    • Li, D.1    Duan, S.2    Hu, Y.3
  • 12
    • 62749130246 scopus 로고    scopus 로고
    • Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol for the synthesis of indenoisoquinolines
    • Jayanth, T. T.; Zhang, L.; Johnson, T. S.; Malinakova, H. C. Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol for the synthesis of indenoisoquinolines Org. Lett. 2009, 11, 815
    • (2009) Org. Lett. , vol.11 , pp. 815
    • Jayanth, T.T.1    Zhang, L.2    Johnson, T.S.3    Malinakova, H.C.4
  • 13
    • 20844460147 scopus 로고    scopus 로고
    • Copper-Catalyzed Cross-Coupling of Imines, Acid Chlorides, and Organostannanes: A Multicomponent Synthesis of α-Substituted Amides
    • Black, D. A.; Arndtsen, B. A. Copper-Catalyzed Cross-Coupling of Imines, Acid Chlorides, and Organostannanes: A Multicomponent Synthesis of α-Substituted Amides J. Org. Chem. 2005, 70, 5133
    • (2005) J. Org. Chem. , vol.70 , pp. 5133
    • Black, D.A.1    Arndtsen, B.A.2
  • 14
    • 33947378709 scopus 로고    scopus 로고
    • Rutaceous alkaloids as models for the design of novel antitumor drugs
    • Tillequin, F. Rutaceous alkaloids as models for the design of novel antitumor drugs Phytochem. Rev. 2007, 6, 65
    • (2007) Phytochem. Rev. , vol.6 , pp. 65
    • Tillequin, F.1
  • 16
    • 7444233119 scopus 로고    scopus 로고
    • Synthesis and Anticancer Activity of Simplified Indenoisoquinoline Topoisomerase i Inhibitors Lacking Substituents on the Aromatic Rings
    • Nagarajan, M.; Morrell, A.; Fort, B. C.; Meckley, M. R.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Synthesis and Anticancer Activity of Simplified Indenoisoquinoline Topoisomerase I Inhibitors Lacking Substituents on the Aromatic Rings J. Med. Chem. 2004, 47, 5651
    • (2004) J. Med. Chem. , vol.47 , pp. 5651
    • Nagarajan, M.1    Morrell, A.2    Fort, B.C.3    Meckley, M.R.4    Antony, S.5    Kohlhagen, G.6    Pommier, Y.7    Cushman, M.8
  • 19
    • 0037011905 scopus 로고    scopus 로고
    • Synthesis of New Dihydroindeno[1,2- c ]isoquinoline and Indenoisoquinolinium Chloride Topoisomerase i Inhibitors Having High in Vivo Anticancer Activity in the Hollow Fiber Animal Model
    • Jayaraman, M.; Fox, B. M.; Hollingshead, M.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Synthesis of New Dihydroindeno[1,2- c ]isoquinoline and Indenoisoquinolinium Chloride Topoisomerase I Inhibitors Having High in Vivo Anticancer Activity in the Hollow Fiber Animal Model J. Med. Chem. 2002, 45, 242
    • (2002) J. Med. Chem. , vol.45 , pp. 242
    • Jayaraman, M.1    Fox, B.M.2    Hollingshead, M.3    Kohlhagen, G.4    Pommier, Y.5    Cushman, M.6
  • 21
    • 34548831094 scopus 로고    scopus 로고
    • Convenient synthesis of indeno[1,2- c ]isoquinolines as constrained forms of 3-arylisoquinolines and docking study of a topoisomerase i inhibitor into DNA-topoisomerase i complex
    • Van, H. T. M.; Le, Q. M.; Lee, K. Y.; Lee, E.-S.; Kwon, Y.; Kim, T. S.; Le, T. N.; Lee, S.-H.; Cho, W.-J. Convenient synthesis of indeno[1,2- c ]isoquinolines as constrained forms of 3-arylisoquinolines and docking study of a topoisomerase I inhibitor into DNA-topoisomerase I complex Bioorg. Med. Chem. Lett. 2007, 17, 5763
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 5763
    • Van, H.T.M.1    Le, Q.M.2    Lee, K.Y.3    Lee, E.-S.4    Kwon, Y.5    Kim, T.S.6    Le, T.N.7    Lee, S.-H.8    Cho, W.-J.9
  • 23
    • 84855731878 scopus 로고    scopus 로고
    • Evaluation of the biological activity of the submitted compounds in high-throughput screens is currently underway, and results will become available via PubChem
    • Evaluation of the biological activity of the submitted compounds in high-throughput screens is currently underway, and results will become available via PubChem (http://www.ncbi.nlm.nih.gov/pccompound).
  • 24
    • 0015417053 scopus 로고
    • Utilization of operational schemes for analog synthesis in drug design
    • Topliss, J. G. Utilization of operational schemes for analog synthesis in drug design J. Med. Chem. 1972, 15, 1006
    • (1972) J. Med. Chem. , vol.15 , pp. 1006
    • Topliss, J.G.1
  • 25
    • 35048815950 scopus 로고    scopus 로고
    • Elements of Regiocontrol in Palladium-Catalyzed Oxidative Arene Cross-Coupling
    • Stuart, D. R.; Villemure, E.; Fagnou, K. Elements of Regiocontrol in Palladium-Catalyzed Oxidative Arene Cross-Coupling J. Am. Chem. Soc. 2007, 129, 12072
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12072
    • Stuart, D.R.1    Villemure, E.2    Fagnou, K.3
  • 26
    • 34848899222 scopus 로고    scopus 로고
    • Catalytic and highly regioselective cross-coupling of aromatic C-H substrates
    • Hull, K. L.; Sanford, M. S. Catalytic and highly regioselective cross-coupling of aromatic C-H substrates J. Am. Chem. Soc. 2007, 129, 11904
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 11904
    • Hull, K.L.1    Sanford, M.S.2
  • 27
    • 36349032389 scopus 로고    scopus 로고
    • Activation: Palladium-Catalyzed Direct Construction of Highly-Fused Heterocyclic Systems
    • Ohno, H.; Iuchi, M.; Fujii, N.; Tanaka, T.; Zipper-Mode Double, C-H Activation: Palladium-Catalyzed Direct Construction of Highly-Fused Heterocyclic Systems Org. Lett. 2007, 9, 4813
    • (2007) Org. Lett. , vol.9 , pp. 4813
    • Ohno, H.1    Iuchi, M.2    Fujii, N.3    Tanaka, T.4    Zipper-Mode Double, C.-H.5
  • 28
    • 21244448893 scopus 로고    scopus 로고
    • Total synthesis of cavicularin and riccardin C: Addressing the synthesis of an arene that adopts a boat configuration
    • Harrowven, D. C.; Woodcock, T.; Howes, P. D. Total synthesis of cavicularin and riccardin C: Addressing the synthesis of an arene that adopts a boat configuration Angew. Chem., Int. Ed. 2005, 44, 3899
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3899
    • Harrowven, D.C.1    Woodcock, T.2    Howes, P.D.3
  • 29
    • 4644360018 scopus 로고    scopus 로고
    • Application of a catalytic palladium biaryl synthesis reaction, via C-H functionalization, to the total synthesis of Amaryllidaceae alkaloids
    • Torres, J. C.; Pinto, A. C.; Garden, S. J. Application of a catalytic palladium biaryl synthesis reaction, via C-H functionalization, to the total synthesis of Amaryllidaceae alkaloids Tetrahedron 2004, 60, 9889
    • (2004) Tetrahedron , vol.60 , pp. 9889
    • Torres, J.C.1    Pinto, A.C.2    Garden, S.J.3
  • 30
    • 0031013608 scopus 로고    scopus 로고
    • Anion-Accelerated Palladium-Catalyzed Intramolecular Coupling of Phenols with Aryl Halides
    • Hennings, D. D.; Iwasa, S.; Rawal, V. H. Anion-Accelerated Palladium-Catalyzed Intramolecular Coupling of Phenols with Aryl Halides J. Org. Chem. 1997, 62, 2
    • (1997) J. Org. Chem. , vol.62 , pp. 2
    • Hennings, D.D.1    Iwasa, S.2    Rawal, V.H.3
  • 31
    • 78650202676 scopus 로고    scopus 로고
    • Palladium-mediated intramolecular o-arylation: A simple route for the synthesis of quino[2,3- c ] and quino[3,2- b ]carbazoles
    • For an example of an intramolecular electrophilic palladation yielding a contiguously tetrasubstituted aromatic ring via the only available regiochemical pathway, see
    • For an example of an intramolecular electrophilic palladation yielding a contiguously tetrasubstituted aromatic ring via the only available regiochemical pathway, see: Sreenivas, D. K.; Nagarajan, R. Palladium-mediated intramolecular o-arylation: a simple route for the synthesis of quino[2,3- c ] and quino[3,2- b ]carbazoles Tetrahedron 2010, 66, 9650
    • (2010) Tetrahedron , vol.66 , pp. 9650
    • Sreenivas, D.K.1    Nagarajan, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.