Wang et al., 2020 - Google Patents

Efficient Arylation of 2, 7-Naphthyridin-1 (2 H)-one with Diaryliodonium Salts and Discovery of a New Selective MET/AXL Kinase Inhibitor

Wang et al., 2020

Document ID
13876315766096515608
Author
Wang M
Xu H
Gong Y
Qu R
Zhuo L
Huang W
Publication year
Publication venue
ACS Combinatorial Science

External Links

Snippet

New 8-chloro-2-phenyl-2, 7-naphthyridin-1 (2 H)-one building blocks bearing diverse substitutes on the 2-phenyl group were synthesized via an efficient diaryliodonium salt- based N-arylation strategy with the advantage of mild conditions, short reaction times, and …
Continue reading at pubs.acs.org (other versions)

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38Nitrogen atoms
    • C07D215/42Nitrogen atoms attached in position 4
    • C07D215/46Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20Oxygen atoms
    • C07D215/22Oxygen atoms attached in position 2 or 4
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D513/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/06Peri-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D221/00Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems ortho- or peri-condensed ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom

Similar Documents

Publication Publication Date Title
Rasheed et al. Copper-catalyzed inter-and intramolecular C–N bond formation: synthesis of benzimidazole-fused heterocycles
Zhao et al. Palladium-catalyzed tandem amination reaction for the synthesis of 4-quinolones
Verma et al. Silver-catalyzed tandem synthesis of naphthyridines and thienopyridines via three-component reaction
Chung et al. Recent advances in research of natural and synthetic bioactive quinolines
Kim et al. Discovery of pyrrolopyridine− pyridone based inhibitors of Met kinase: Synthesis, X-ray crystallographic analysis, and biological activities
Ravi et al. Transition-metal-free C-3 arylation of quinoline-4-ones with arylhydrazines
Audisio et al. A general copper powder-catalyzed Ullmann-type reaction of 3-halo-4 (1 H)-quinolones with various nitrogen-containing nucleophiles
Zou et al. Copper-catalyzed ring-opening/reconstruction of anthranils with oxo-compounds: synthesis of quinoline derivatives
Morrell et al. Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors
Kato et al. Novel strategy for synthesis of substituted benzimidazo [1, 2-a] quinolines
Lv et al. Design, synthesis, and antihepatitis B virus activities of novel 2-pyridone derivatives
Inglis et al. Identification and specificity studies of small-molecule ligands for SH3 protein domains
He et al. Visible-Light-Induced Direct Difluoroalkylation of Uracils, Pyridinones, and Coumarins
Cinelli et al. Design, synthesis, and biological evaluation of 14-substituted aromathecins as topoisomerase I inhibitors
Wang et al. Efficient Arylation of 2, 7-Naphthyridin-1 (2 H)-one with Diaryliodonium Salts and Discovery of a New Selective MET/AXL Kinase Inhibitor
Lin et al. Tandem synthesis of pyrrolo [2, 3-b] quinolones via cadogen-type reaction
Dhiman et al. Rh (III)-catalyzed C (8)–H activation of quinoline N-Oxides: regioselective C–Br and C–N bond formation
Thompson et al. Synthesis and Structure− Activity Relationships of 7-Substituted 3-(2, 6-Dichlorophenyl)-1, 6-naphthyridin-2 (1 H)-ones as Selective Inhibitors of pp60 c-src
Cross et al. Divergent route to access structurally diverse 4-quinolones via mono or sequential cross-couplings
Pang et al. Copper-catalyzed tandem aerobic oxidative cyclization for the synthesis of polysubstituted quinolines via C (sp3)/C (sp2)–H bond functionalization
Kim et al. Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3+ 2] Cycloaddition
Collet et al. Modular three-component synthesis of 4-aminoquinolines via an imidoylative Sonogashira/cyclization cascade
Liu et al. CuX-Activated N-Halosuccinimide: Synthesis of 3-Haloquinolines via Electrophilic Cyclization of Alkynyl Imines
Kumar et al. Chemoselective Azidation of o-Alkynylaldehydes over [3+ 2] Cycloaddition and Subsequent Staudinger Reaction: Access to Benzonaphthyridines/Naphthyridines
Kumar et al. Pd-catalyzed one-Pot stepwise synthesis of benzo [b][1, 6] naphthyridines from 2-chloroquinoline-3-carbonitriles using sulfur and amines as nucleophiles