α‐Haloamide Reactions: IV [1]. A New Sodium Amidepromoted Rearrangement of α‐Haloacetamides into Ureas

Sarel, Shalom; D’Angeli, Ferruccio; Klug, J. T.; Taube, A.

doi:10.1002/ijch.196400045

Cited by 11 publications

(4 citation statements)

References 9 publications

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“…To complete the scenario D'Angeli and co‐workers in 1964 disclosed a rearrangement reaction competing with the Favorskii‐like one, occurring when the N ‐cyclohexyl‐α‐chloro‐α,α‐diphenylacetamide A reacted with NaNH 2 in liquid ammonia. They reported that the reaction furnished the N 1‐cyclohexyl‐ N 1‐benzhydrylurea C as the predominant product (Scheme ).…”

Section: Aziridinones Ring‐forming/ring‐opening Processesmentioning

confidence: 99%

The Fascinating Chemistry of α‐Haloamides

et al. 2020

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The aim of this review is to highlight the rich chemistry of α‐haloamides originally mainly used to discover new C−N, C−O and C−S bond forming reactions, and later widely employed in C−C cross‐coupling reactions with C(sp3), C(sp2) and C(sp) coupling partners. Radical‐mediated transformations of α‐haloamides bearing a suitable located unsaturated bond has proven to be a straightforward alternative to access diverse cyclic compounds by means of either radical initiators, transition metal redox catalysis or visible light photoredox catalysis. On the other hand, cycloadditions with α‐halohydroxamate‐based azaoxyallyl cations have garnered significant attention. Moreover, in view of the important role in life and materials science of difluoroalkylated compounds, a wide range of catalysts has been developed for the efficient incorporation of difluoroacetamido moieties into activated as well as unactivated substrates.

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Section: Aziridinones Ring‐forming/ring‐opening Processesmentioning

confidence: 99%

The Fascinating Chemistry of α‐Haloamides

et al. 2020

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“…pAa Determination.-The ionization constants of dinitro-2pyridylalanylglycine and dinitro -2-pyridylalanine were determined by a photometric method. All spectral measurements were made with a Model DU Beckman spectrophotometer in sulfuric acid solution at 25°; temperature control was main- (3) Chromatographically pure. (4) F. Sanger, Biochem.…”

Section: Ahmentioning

confidence: 99%

The Intramolecular Participation of the Pyridyl Group in the Acid Hydrolysis of Dinitropyridyl Dipeptides

Signor¹

1965

J. Org. Chem.

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“…We describe possible intermediates that explain the high reactivity of these tertiary halides toward substitution. [14][15][16][17] Overall, we anticipate that this method, which is operationally simple and uses readily available, low-toxicity reagents, will be adaptable to the radiosynthesis of (pre)clinical PET imaging doses. [18,19]…”

Section: Introductionmentioning

confidence: 99%

Zinc‐Mediated Radiosynthesis of Unprotected Fluorine‐18 Labelled α‐Tertiary Amides

Wright,

Ma,

Webb

et al. 2023

Angewandte Chemie

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This report describes the development of a Zn(OTf)2‐mediated method for converting α‐tertiary haloamides to the corresponding fluorine‐18 labelled α‐tertiary fluoroamides with no‐carrier‐added [18F]tetramethylammonium fluoride. 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene is an essential additive for achieving high radiochemical conversion. Under the optimised conditions, radiofluorination proceeds at sterically hindered tertiary sites in high radiochemical conversions, yields, and purities. This method has been successfully automated and applied to access >200 mCi (>7.4 GBq) of several model radiofluorides. Mechanistic studies led to the development of a new, nucleophilic C−H radiofluorination process using N‐sulphonyloxyamide substrates.

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α‐Haloamide Reactions: IV [1]. A New Sodium Amidepromoted Rearrangement of α‐Haloacetamides into Ureas

Cited by 11 publications

References 9 publications

The Fascinating Chemistry of α‐Haloamides

The Fascinating Chemistry of α‐Haloamides

The Intramolecular Participation of the Pyridyl Group in the Acid Hydrolysis of Dinitropyridyl Dipeptides

Zinc‐Mediated Radiosynthesis of Unprotected Fluorine‐18 Labelled α‐Tertiary Amides

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