Beckmann Rearrangement of the Oximes of Phenyl 2-Pyridyl Ketone (2-Benzoylpyridine)

Huntress, Ernest H.; Walter, Henry C.

doi:10.1021/ja01191a046

Cited by 56 publications

(18 citation statements)

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“…N‐(3‐pyridine)tridecanoylamide was obtained by a Beckmann rearrangement reaction catalyzed by thionyl chloride . According to the reaction's procedure, a mixture containing chloroform, ( E) ‐oxime of 1‐(3‐pyridyl)tridecan‐1‐one and thionyl chloride was boiled under reflux for 6 h. The liquid obtained after evaporation of chloroform was dissolved in ethanol and the solution was made alkaline with NaOH.…”

Section: Methodsmentioning

confidence: 99%

Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane

Wieszczycka

Zembrzuska

2015

Photochem & Photobiology

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The goal of the research was to study the reactivity of the hydrophobic 2- and 3-pyridineketoximes under exposure to UV-VIS light. The photodegradation was conducted in both toluene and heptane for 10 h under atmosphere of argon. Ten-hour irradiation experiments demonstrated that the pyridineketoximes underwent the facile E-Z photoisomerization, photo-Beckmann rearrangement, and to a lesser extent, the photosubstitution to the pyridine ring. From LC-MS and NMR analysis of the irradiated solutions, it was found that the photosubstitution proceeded to give the corresponding 6-substituted 2- or 3-pyridylketoxime via the replacement of the ring hydrogen by the benzyl or heptyl group. The photo-Beckmann rearrangement led to the formation of the corresponding amides, but also other products formed in the photo-decomposition reaction.

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Section: Methodsmentioning

confidence: 99%

Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane

Wieszczycka

Zembrzuska

2015

Photochem & Photobiology

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“…The two isomers of phenyl-2-pyridyl ketoxin~e were prepared, separated, and purified after the method of Huntress and Walter (32). The melting point of the syn-phenyl isomer was 153.0-153.5 "C; that of the alzti-phenyl form was 167.0-167.5 "C. (Literature values (32) 150.5-152.5 "C and 16.5-167 "C respectively.…”

Section: Reagentsmentioning

confidence: 99%

The Copper(ii) Syn-Phenyl-2-Pyridyl Ketoxime System Part I

Meek¹,

Cheney²

1965

Can. J. Chem.

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“…The Beckmann rearrangement 26 , 27 is a classical way to afford anilines from ketoximes or surrogates. A pioneering work reported by Walter 28 relied on a similar strategy starting from 2-benzoylpyridine ketoxime or its O - p -toluenesulfonate, followed by a Beckmann rearrangement and hydrolysis to provide 2-amino pyridine or anilines, but only a limited number of examples were presented. A recent patent 29 described anilines synthesis using the Beckmann rearrangement of aryl ketoximes, which still needed conc.…”

Section: Introductionmentioning

confidence: 99%

Hydroxylamine-mediated C–C amination via an aza-hock rearrangement

et al. 2021

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Despite the widespread use of anilines, synthetic challenges to these targets still exist. Selectivity is often an issue, when using the traditional nitration-reduction sequence or more modern approaches, including arene C–H aminations catalyzed by transition metals, photosensitizers, or electrodes. Accordingly, there is still a need for general methods to rapidly, directly access specific isomers of substituted anilines. Here, we report a simple route towards the synthesis of such motifs starting from benzyl alcohols, which are converted to anilines by the use of arylsulfonyl hydroxylamines, via an aza-Hock rearrangement. Good to excellent yields are observed. The method is applicable to various benzyl alcohol surrogates (such as ethers, esters, and halides) as well as simple alkylarenes. Functionalizations of pharmaceutically relevant structures are feasible under the reaction conditions. Over ten amination reagents can be used, which facilitates the rapid assembly of a vast set of compounds.

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Beckmann Rearrangement of the Oximes of Phenyl 2-Pyridyl Ketone (2-Benzoylpyridine)

Abstract: polymer particles the rate of polymerization of styrene is proportional to the number of polymer particles present and is in dependent of the persulfate concentration. This can best be interpreted as indicating that the average number of free

Cited by 56 publications

References 0 publications

Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane

Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane

The Copper(ii) Syn-Phenyl-2-Pyridyl Ketoxime System Part I

Hydroxylamine-mediated C–C amination via an aza-hock rearrangement

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