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A facile synthesis of (iso)quinolinyl-3(2H)-furanones from (iso)quinoline N-oxides and 1,4-diyn-3-ones in the presence of copper catalyst or under metal-free conditions was developed. The resulting (iso)quinolinyl-3(2H)-furanones could be easily converted to (iso)quinolinyl-isoxazoles, pyrazoles and polycyclic (iso)quinoline derivatives. In addition, the success in one-pot, metal-free synthesis of isoquinolinyl-3(2H)-furanone starts from isoquinoline shows the capacity of this method for the metal-free derivatization of pyridine, quinoline and isoquinoline. (Figure presented.).

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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H-phosphonate-mediated amination of quinoline N-oxides with tertiary amines: A mild and metal-free synthesis of 2-dialkylaminoquinolines

A synthetic strategy has been developed for the synthesis of 2-dialkylaminoquinolines from easily available quinoline N-oxides, tertiary amines, diisopropyl H-phosphonate and carbon tetrachloride (CCl4) in one pot under metal-free conditions at room temperature.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H452N – PubChem

 

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Transition-metal-catalyzed reactions involving reductive elimination between dative ligands and covalent ligands

Reductive elimination is a crucial bond-forming elementary reaction in various transition-metal mediated reactions. Apart from the well-developed classic reductive elimination, the non-classic reductive elimination occurring between a covalent ligand and a dative ligand, which has been known for over 50 years, has gradually attracted much attention from the organic community. By avoiding ppi-dpi repulsion between the filled metal d-orbital and the filled ligand p-orbital and forming a cationic-type molecule, non-classic reductive elimination could facilitate many catalytic reactions that were difficult to be realized via classic reductive elimination. In this review, transition-metal catalyzed C-P, C-S, C-N, and C-C bond-forming reactions with non-classic reductive elimination as the key elementary step are summarized.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H517N – PubChem

 

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Copper-catalyzed direct C-H phosphorylation of: N -imino isoquinolinium ylides with H-phosphonates

A new and efficient protocol for the synthesis of phosphorus-containing isoquinoline skeletons via copper-catalyzed direct C-H phosphorylation of N-iminoisoquinolinium ylides with H-phosphonates has been described. A variety of N-iminoisoquinolinium ylides reacted under the ligand and oxidant free conditions smoothly to afford phosphorylated isoquinolines in moderate to excellent yields.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H713N – PubChem

 

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External-Photocatalyst-Free Visible-Light-Mediated Synthesis of Indolizines

A visible-light-mediated synthesis of valuable polycyclic indolizine heterocycles from easily accessed brominated pyridine and enol carbamate derivatives has been developed. This process, which operates at room temperature under irradiation from readily available light sources, does not require the addition of an external photocatalyst. Instead, an investigation into the reaction mechanism indicates that the indolizine products themselves may be in some way involved in mediating and accelerating their own formation. Preliminary studies also show that these simple heterocyclic compounds may be capable of facilitating other visible-light-mediated transformations.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H618N – PubChem

 

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Distortions of a flexible metal-organic framework from substituted pendant ligands

Four new variants of the 1,4-benzenedicarboxylate MIL-53 structure have been prepared for CoII under solvothermal conditions and their structures solved and refined from single-crystal X-ray data. All materials contain pendant pyridine-N-oxide ligands that bridge pairs of CoII atoms in the inorganic backbone of the structure via O. By the use of the ligands 3-bromopyridine-N-oxide, 4-methoxypyridine-N-oxide, isoquinoline-N-oxide and 4-phenylpyridine-N-oxide, materials are prepared with the same topology but distinct structures. These illustrate how the MIL-53 structure is able to distort to accommodate the bulk of the various substituents on the pyridine ring. The bulkiest pendant ligand, 4-phenylpyridine-N-oxide, results in a distortion of the diamond-shaped channels in an opposite sense to that seen previously in expanded forms of the parent MIL-53 structure. By comparison with published crystal structures for MIL-53 with various occluded guests, the structural distortions that take place to accommodate the pendant ligands are quantified and it is shown how a twisting of the 1,4-benzenedicarboxylate ligand, instead of a hinging about the mu2-carboxylate-metal connection, allows the new structures that are observed.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H587N – PubChem

 

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Green and reusable synthetic procedure for pyridine N-oxides catalyzed by a lacunary polyoxometalate

A lacunary Keggin polyoxometalate of K8[BW11O39H] · 13H2O was used as an effective and reusable catalyst for pyridine oxidation. Good yields of pyridine N-oxides were obtained in this catalytic system with hydrogen peroxide in water under mild conditions. Taylor and Francis Group, LLC.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H720N – PubChem

 

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Palladium-catalyzed external-oxidant-free coupling reactions between isoquinoline/quinoline N-oxides with olefins

A convenient and efficient approach for the synthesis of 1-alkenylisoquinolines and 2-alkenylquinolines was developed via palladium-catalyzed coupling reactions between isoquinoline/quinoline N-oxides with olefins under external-oxidant-free conditions. Biological evaluation revealed that some of the obtained 1-alkenylisoquinolines exhibited in vitro antiproliferative activities on human-derived prostate, breast, esophageal, and stomach cancer cell lines.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Nickel-promoted C(2)-H amidation of quinoline: N -oxides with N -fluorobenzenesulfonimide

Reported herein is an unprecedented nickel-promoted C-H amidation reaction of quinoline N-oxides using N-fluorobenzenesulfonimide (NFSI) as the amination reagent. This strategy provides a convenient access to a variety of useful 1,2-dihydro-2-iminoquinolines in moderate to good yields. Notable advantages of this protocol include easy operation and mild reaction conditions.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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PREPARATION OF HETEROARENECARBONITRILES BY REACTION OF HETEROARENE N-OXIDES WITH TRIMETHYLSILYL CYANIDE IN THE PRESENCE OF DBU

Several heteroarenecarbonitriles were prepared from the corresponding heteroarene N-oxides by treatment with trimethylsilylcyanide (TMSCN) in the presence of a base in tetrahydrofuran (THF). 1,8-Diazabicyclo<5.4.0>-7-undecene (DBU) was found to be an effective base for the cyanation.

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Reference£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H582N – PubChem