Quinoline nitroxide radicals. Ipso-attack in the reaction between 2-methoxy and 2-cyanoquinoline N-oxide, and phenylmagnesium bromide

doi:10.1002/JHET.5570170217

Paper

Quinoline nitroxide radicals. Ipso-attack in the reaction between 2-methoxy and 2-cyanoquinoline N-oxide, and phenylmagnesium bromide

Published Mar 1, 1980 · M. Colonna, L. Greci, M. Poloni

Journal of Heterocyclic Chemistry

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7

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0

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Abstract

2-Methoxy and 2-cyanoquinoline N-oxide, when treated with phenylmagnesium bromide, undergo a nucleophilic ipso-attack at C-2, yielding, by elimination of methoxymagnesium bromide or cyanomagnesium bromide, the corresponding 2-phenylquinoline N-oxides, which react with the excess of Grignard reagents forming 2,2-diphenylquinoline 1-oxyls. Even when the methoxy and cyano groups are in position 4, the attack by the Grignard reagent takes place at C-2 giving 2-phenylquinolines and 2-phenylquinoline N-oxides by elimination of hydroxymagnesium bromide and bromomagnesium hydride, respectively; the formation of 2,2-diphenylquinoline l-oxyls in these reactions is discussed.

Study Snapshot

Ipso-attack at C-2 in the reaction between 2-methoxy and 2-cyanoquinoline N-oxide, and phenylmagnesium bromide, leads to 2-phenylquinoline N-oxides, which can form 2,2-diphenylquinoline 1-oxyls.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Quinoline nitroxide radicals. Ipso-attack in the reaction between 2-methoxy and 2-cyanoquinoline N-oxide, and phenylmagnesium bromide

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References

The 1H NMR spectra of quinoline, quinoline N‐oxide, the quinolinium ion and of their monomethyl derivatives

The same effects that affect protons shielding in heterocyclic systems also affect the proton chemical shift of methyl groups in monomethyl derivatives, with vicinal coupling constants rationalized based on -electron bond order and neighboring atoms' electro-negativity.

Stable nitroxide radicals from 2-substituted quinoline-N-oxides with organometallic compounds

Stable nitroxide radicals can be obtained by oxidizing 2-substituted quinoline-N-oxides with organometallic compounds, but their solid state isolation remains unresolved.

Aromatic azocompounds—VI

The aromatic arylation of ortho-substituted azobenzenes with phenylmagnesium bromide produces 2-phenyl-6-methyl- and 2-methoxy-2′-methyl-6′-phenyl-azobenzene, with larger substituents reducing reactivity

The mechanism of an unusual reaction of ortho-substituted azobenzenes with grignard reagents

The unusual reaction of ortho-substituted azobenzenes with Grignard reagents involves 1,4-addition and magnesium bromohydride elimination, leading to 2-methoxy-2′,6′-diaryl- and 2-methyl-6-aryl-azobenzene

Heilmittelchemische Studien in der heterocyclischen Reihe. 24. Mitteilung. Über die Umlagerung heterocyclischer N-Oxyde mit Trifluor-acetanhydrid

Trifluoroacetic anhydride effectively reorganizes heterocyclic N-oxides into nuclear oxygenated heterocycles, resulting in 2-Cyanoquinol-4-one and 3-hydroxy-4-cyanoquinoline.

Citations

Visible-Light Promoted C2 Selective Arylation of Quinoline and Pyridine N-Oxides with Diaryliodonium Tetrafluoroborate.

Visible-light promoted C2 selective arylation of quinoline and pyridine N-oxides with diaryliodonium tetrafluoroborate, using eosin Y as a photo-catalyst, efficiently synthesizes 2-aryl substituted

The development of carbene-stabilized N–O radical coupling strategy in metal-free regioselective C–H azidation of quinoline N-oxides

This study developed an efficient oxidative C2–H azidation of quinoline N-oxides with TMSN3, involving a novel carbene-stabilized N-O radical intermediate, which can be scaled up to gram-synthesis and converted into other functional heterocycles.

Indolenine Oxides, VIII. Reaction of 5,7-di-tert-butyl-3,3-dimethyl-3H-indole 1-Oxide with Grignard Reagents. – A New Stable Aminyl Oxide (Nitroxide)

The Grignard reaction efficiently converts Indolenine Oxide 1 into its 2-substituted derivatives, yielding a new stable aminyl oxide (nitroxide) with high yields.

STABLE NITROXIDE RADICALS. REACTION BETWEEN 2-CYANO- AND 4-CYANOBENZOQUINOLINE N-OXIDES AND THE GRIGNARD REAGENT

Stable nitroxide radicals can be obtained from 2-cyano- and 4-cyano-benzoquinoline N-oxides and the Grignard reactant, with elimination of bromomagnesium hydride and cyanomagnesium bromide.

Electrochemical behaviour of heterocyclic amine derivatives in media with controlled proton availability: Part III. Reduction mechanism and electron spin resonance study of cyanoquinolines and their N-oxides in DMF

Cyanoquinolines and their N-oxides undergo two monoelectronic steps in dimethylformamide, while quinoline-1-oxides undergo three reduction steps, with substituents influencing the electrode process direction.