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Tetraphenylporphiratoiron (II), a model complex of reduced cytochrome P-450, reduces several substrates such as tertiary amine N-oxides and arene oxides at room temperature in anaerobic conditions.A process for the direct oxene transfer from oxide to reduced iron porphyrin is suggested.KEYWORDS – cytochrome P-450; reduction; deoxygenation; tertiary amine N-oxide; tetraphenylporphinatoiron (II); oxene transfer; arene oxide; ferryl oxide

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Isoquinoline – Wikipedia,
Isoquinoline | C9H583N – PubChem

 

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Purpose. A systematic study to assess the influence of N-oxygenation on the lipophilicity of aromatic weak bases was performed. Methods. The methods used were experimental (CPC and shake-flask techniques) and computational (AMI semi-empirical method). Results. The intrinsic increment in the log P(oct) system for an oxygen atom added to form an aromatic N-oxide, designated as diff(log P(N(O)-N)), was -1.91, but the presence of para-substituents markedly affected this value. The good linear relationship (r2 = 0.92) between diff(log P(N(O)-N)), and the electronic density on the oxygen atom suggests that H-bond acceptor basicity is the main structural factor responsible for the variations in lipophilicity of aromatic N-oxides. Partition coefficients of aromatic N-oxides in dodecane/buffer and chloroform/buffer systems also support this hypothesis. Conclusions. The solvent-dependent polarity of the N-oxide moiety is mainly due to its marked H-bond acceptor basicity.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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The first example of electrochemical deoxygenative C2 arylation of quinoline N-oxides using sulfonyl hydrazines was demonstrated in this work. By employing both anodic oxidation and cathodic reduction, a variety of 2-arylquinolines were synthesized under metal catalyst-, exogenous-oxidant-, and exogenous-reductant-free conditions.

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N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero)aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Metal-free methylation of a pyridine N-oxide C-H bond was developed using peroxide as a methyl reagent under neat conditions. Pyridine N-oxide derivatives with various groups (e.g., Cl, NO2, and OCH3) were all suitable substrates, and the desired products were obtained in moderate to excellent yields under standard conditions. Moreover, the methylation can be performed with a good yield on the gram-scale experiment. Tentative mechanistic studies show that the methylation is a classical radical process.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H543N – PubChem

 

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Reference of 1532-72-5, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.1532-72-5, Name is Isoquinoline N-Oxide, molecular formula is C9H7NO. In a article,once mentioned of 1532-72-5

Decarboxylative cross-coupling reactions of substituted 2-carboxyazine N-oxides, with a variety of (hetero)aryl halides, by bimetallic Pd 0/CuI and Pd0/AgI catalysis are reported. Two possible pathways, a conventional bimetallic-catalyzed decarboxylative arylation, as well as a protodecarboxylative/direct C-H arylation sequence have been considered. These methods provide the first general decarboxylative arylation methodology for the 2-carboxyazine series. Choose your pathway: Decarboxylative cross-coupling reactions of substituted 2-carboxyazine N-oxides, with a variety of (hetero)aryl halides, by bimetallic Pd0/CuI and Pd0/AgI catalysis are reported (see figure). These methods provide the first general decarboxylative arylation methodology in the 2-carboxyazine series.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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The irradiation of isoquinoline N-oxide in ethanol resulted in the formation of lactam in a ca.67percent yield via the S1 state (Process I).When the photochemical isomerization was carried out in the presence of a magnetic field, the chemical yield of lactam was found to show a minimum at approximately 1T.In order to interpret this new phenomenon, Process I was assumed to be initiated by electron transfer from the excited singlet N-oxide to the hydrogen-bonded ethanol (the formation of a singlet hydrogen-bonded radical ion pair).Thus, the new type of magnetic-field effect was excellently explained in terms of an electron-nuclear hyperfine interaction mechanism including the electron-exchange interaction in the radical-ion pair (the magnetic-field effect due to HFI-J mechanism).This implies that the magnetic-field effect is unambiguous evidence that Process I (N-oxide – lactam) does not involve the oxaziridine intermediate, but proceeds via the singlet hydrogen-bonded radical-ion pair (radical-ion-pair mechanism of Process I).The irradiation of 1-cyanoisoquinoline N-oxide in ethanol resulted in the formation of 1,3-oxazepine in a ca. 66percent yield via the S1 state (Process II).The photochemical isomerization was not affected at all by an external magnetic field.This is consistent with the idea that Process II (N-oxide – oxazepine) does not involve a field-sensitive intermediate, but occurs with the intervention of oxaziridine (the oxaziridine mechanism of Process II).

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Organocatalytic functionalization of heteroaromatic N-oxides was investigated using in situ generated onium amide bases, and C-nucleophiles were efficiently introduced by the sequential addition-elimination reaction under metal-free conditions, affording 2-substituted nitrogen heteroaromatics generally in good to high yields. The Royal Society of Chemistry 2013.

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Isoquinoline – Wikipedia,
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We report herein that symmetrical and non-symmetrical N-heterobiaryls are produced by a potassium tert-butoxide-mediated dimerization of heterocyclic N-oxides. The reaction is scalable and transition metal-free, and can be carried out under thermal and microwave conditions. Preliminary mechanistic studies point to the involvement of radical anionic intermediates arising from the N-oxide substrates and potassium tert-butoxide.

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A simple synthetic strategy has been developed for the synthesis of 2- and 1-alkyl/aryl/dialkylaminoquinolines and isoquinolines from the easily available quinoline and isoquinoline-N-oxides, different amines, triflic anhydride as activating agent and acetonitrile as solvent in a one-pot reaction under metal-free conditions at 0 C to room temperature.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem