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Allylation of aromatic aldehydes 1a-m with allyl- and crotyl- trichlorosilanes 2-4, catalyzed by the chiral N-oxide QUINOX (9), has been found to exhibit a significant dependence on the electronics of the aldehyde, with p-(trifluoromethyl)benzaldehyde 1g and its p-methoxy counterpart 1h affording the corresponding homoallylic alcohols 6g,h in 96 and 16% ee, respectively, at -40C. The kinetic and computational data indicate that the reaction is likely to proceed via an associative pathway involving neutral, octahedral silicon complex 22 with only one molecule of the catalyst involved in the rate- and selectivity-determining step. The crotylation with (E) and (Z)-crotyltrichlorosilanes 3 and 4 is highly diastereoselective, suggesting the chairlike transition state 5, which is supported by computational data. High-level quantum chemical calculations further suggest that attractive aromatic interactions between the catalyst 9 and the aldehyde 1 contribute to the enantiodifferentiation and that the dramatic drop in enantioselectivity, observed with the electron-rich aldehyde 1h, originates from narrowing the energy gap between the (R)- and (S)-reaction channels in the associative mechanism (22). Overall, a good agreement between the theoretically predicted enantioselectivities for 1a and 1h and the experimental data allowed to understand the specific aspects of the reaction mechanism.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Various pyridine, quinoline, isoquinoline, and pyrimidine N-oxides were converted to their corresponding alpha-N-aryltriflamidoheteroarenes in good yield by treatment with N-aryltriflimides, both neat and in solution, at temperatures ranging from rt to 100 C.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H532N – PubChem

 

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 1532-72-5, name is Isoquinoline N-Oxide, introducing its new discovery. COA of Formula: C9H7NO

A process for the production of aromatic heterocyclic N-oxides by reaction between an aromatic compound comprising a heterocyclic nitrogen atom and hydrogen peroxide in the presence of a manganese porphyrin catalyst is provided. The manganese porphyrin catalyst is substituted by an aromatic group at each meso-position, the aromatic nuclei of the aromatic substituents being substituted by one or more electron-withdrawing groups and/or comprising an aromatic quaternary ammonium heteroatom in the aromatic ring. Preferably, the manganese porphyrin catalyst is manganese tetrakis (2,6-dichlorophenyl) porphyrin chloride, manganese tetrakis (2,6-dichlorophenyl-4-sulphonic acid) porphyrin chloride, manganese tetrakis (4-methylpyridinium) porphyrin chloride, or manganese tetrakis (pentafluorophenyl) porphyrin chloride.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H394N – PubChem

 

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A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H606N – PubChem

 

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Substituted heteroaromatic compounds, especially those based on pyridine, hold a privileged position within drug discovery and medicinal chemistry. However, functionalisation of the C2 position of 6-membered heteroarenes is challenging because of (a) the difficulties of installing a halogen at this site and (b) the instability of C2 heteroaryl-metal reagents. Here we show that C2-alkenylated heteroaromatics can be accessed by simple Br°nsted acid catalysed union of diverse heteroarene N-oxides with alkenes. The approach is notable because (a) it is operationally simple, (b) the Br°nsted acid catalyst is cheap, non-toxic and sustainable, (c) the N-oxide activator disappears during the reaction, and (d) water is the sole stoichiometric byproduct of the process. The new protocol offers orthogonal functional group tolerance to metal-catalysed methods and can be integrated easily into synthetic sequences to provide polyfunctionalised targets. In broader terms, this study demonstrates how classical organic reactivity can still be used to provide solutions to contemporary synthetic challenges that might otherwise be approached using transition metal catalysis.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H462N – PubChem

 

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An economic and eco-friendly straightforward synthesis of highly diversified N-acylated 2-aminoquinolines is successfully achieved via Br°nsted acidic ionic liquid-promoted amidation of quinoline N-oxides with nitriles. The advantage of this present process is highlighted by its easily accessible starting materials, excellent functional group tolerance, 100% atom economy, operational simplicity, and clean reaction profile.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H682N – PubChem

 

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An efficient and concise one-pot strategy for the direct alkylation of quinoline N-oxides via palladium-catalyzed dual C-H bonds activation has been developed. This methodology provides quinoline-containing heterocyclic molecules in moderate to excellent yields. Copyright

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H677N – PubChem

 

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An efficient and convenient procedure for the conversion of pyridine N-oxides to tetrazolopyridines by treatment with 4-toluene sulfonyl chloride and sodium azide in toluene at elevated temperature is described.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H553N – PubChem

 

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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:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 1532-72-5, name is Isoquinoline N-Oxide, introducing its new discovery. SDS of cas: 1532-72-5

Sodium hypophosphite catalytic transfer hydrogenation in the presence of 10percent palladium on carbon constitutes a simple and excellent deoxygenation method for heteroaromatic N-oxides in acetic acid medium.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H432N – PubChem