Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions.

@article{Brodnik2016SynthesisO8,
  title={Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions.},
  author={Helena Brodnik and Franc Po{\vz}gan and Bogdan {\vS}tefane},
  journal={Organic \& biomolecular chemistry},
  year={2016},
  volume={14 6},
  pages={
          1969-81
        }
}
A series of 8-heteroaryl substituted quinolines were prepared, either by direct C-H arylation of five-membered heteroarenes, or Pd-catalyzed coupling of organoboron reagents with bromoquinolines. The use of (benzo)thiophenyl or (benzo)furanyl boron coupling partners allowed further C-H functionalization on the five-membered heteroaryl ring with aryl bromides in one flask to access a variety of polyconjugated molecular architectures. The developed methodology represents a simple approach towards… 
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References

SHOWING 1-10 OF 76 REFERENCES
Synthesis of 8-arylquinolines via one-pot Pd-catalyzed borylation of quinoline-8-yl halides and subsequent Suzuki-Miyaura coupling.
A one-pot process has been developed for the synthesis of 8-arylquinolines via Pd-catalyzed borylation of quinoline-8-yl halides and subsequent Suzuki-Miyaura coupling with aryl halides using
Nickel-catalyzed reaction of arylzinc reagents with N-aromatic heterocycles: a straightforward approach to C-H bond arylation of electron-deficient heteroaromatic compounds.
TLDR
The reaction of electron-deficient N-heteroaromatic compounds, such as pyridines and quinolines, with arylzinc reagents in the presence of a catalytic amount of a nickel complex affords the arylated products, exhibiting a reactivity complementary to conventional direct arylation through electrophilic substitution.
Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.
Palladium-catalyzed direct C-H arylation of N-iminopyridinium ylides provides a powerful and versatile method for the synthesis of functionalized piperidines in good yields. Chemoselective
Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation.
TLDR
A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed and could be converted into aryLacetonitriles with up to 88% yield.
Palladium-Catalysed Direct Arylation of Heteroaromatics with Functionalised Bromopyridines
The regioselective 5-arylation of a variety of heteroaromatics with functionalised pyridyl bromides using palladium catalyst gives a simple access to functionalised heteroarylated pyridines. The
Synthesis of polysubstituted imidazo[1,2-a]pyridines via microwave-assisted one-pot cyclization/Suzuki coupling/palladium-catalyzed heteroarylation.
A new and efficient method for the synthesis of 2,3,6-trisubstituted imidazo[1,2-a]pyridine derivatives using a microwave-assisted one-pot, two-step Suzuki/heteroarylation or one-pot, three-step
A microwave-assisted nucleophilic substitution reaction on a quinoline system: the synthesis of amino analogues of nitroxoline
Abstract A reliable protocol for the synthesis of a series of 8-amino analogues of pharmacologically interesting nitroxoline (5-nitro-8-hydroxyquinoline) is described. The unprecedented displacement
Synthesis of 6-Substituted Phenanthridine Derivatives by Palladium-Catalysed Domino Suzuki–Miyaura/Aza-Michael Reactions
An efficient method for the synthesis of 6-substituted phenanthridine derivatives has been developed through a one-pot process involving a sequence of palladium-catalysed Suzuki–Miyaura reaction
Copper-catalyzed direct C arylation of heterocycles with aryl bromides: discovery of fluorescent core frameworks.
TLDR
The reaction shows excellent regioselectivity and exhibits good functional group tolerance, and the 8-aryl xanthines exhibit fluorescence in a variety of solvents and show promise as reagents for biological imaging.
Rh(I)-catalyzed direct arylation of azines.
TLDR
The Rh(I)-catalyzed direct arylation of azines has been developed and electron-deficient and electron-rich aromatic bromides couple in good yields, and hydroxyl, chloro, fluoro, trifluoromethyl, ether, and ketone functionalities are compatible with the reaction conditions.
...
1
2
3
4
5
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