The facile oxidation of phenacyl bromides with N,N-dialkylhydroxylamines

Gunn, V. E.; Jean, P.

doi:10.1021/jo00424a040

Cited by 20 publications

(10 citation statements)

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“…The structure of 10a appears to be unequivocal, especially since it is clearly a different compound from the N-(0-aminobeiizoyl) isomer (lla), which can be obtained by reaction of inethyl o-aminobeiizoate with liydroxylamine (8). This 0-aroylation of hydroxylaniine by isatoic anhydride evidently involves nucleophilic attack by the hydroxyl group, although formation and rearrangement of an N-oxide, via nucleophilic attack by the amino group, is feasible (9). However if the latter mechanism was operative during the reaction of 7 with hydroxylamine, the stable N-aroyl derivative ( l l a ) would arise and not the observed product 100.…”

Section: Fitzroy D Eddy Keith Vaughan Et Malcolm F G Stevens Canmentioning

confidence: 98%

Anthraniloylanthranilamide (o-amino-N-(o-carbamoylphenyl)benzamide): Preparation and use as a synthetic precursor for quinazolino[1,2,3]benzotriazinones

Eddy¹,

Vaughan²,

Stevens³

1978

Can. J. Chem.

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Several synthetic routes to anthraniloylanthranilamide (6) are described; the problems involved in o-aminobenzoylation reactions are explored. Reduction of N-(o-nitrobenzoyl)anthranilamide by stannous chloride gave a low yield of 6, which was also obtained in low yield by reaction of isatoic anhydride with o-aminobenzamide. The possible use of O-(o-aminobenzoyl)hydroxylamines for o-aminobenzoylation was investigated but proved impractical. Diazotisation of 6 affords 3-(o-carbamoylphenyl)-1,2,3-benzotriazin-4(3H)-one (2), which undergoes base-catalysed cyclisation to the quinazolino[3,2-c]benzotriazine (4). The conversion 2 → 4 probably involves the isomeric quinazolino[1,2-c]benzotriazine (3), which could not be isolated.

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Section: Fitzroy D Eddy Keith Vaughan Et Malcolm F G Stevens Canmentioning

confidence: 98%

Anthraniloylanthranilamide (o-amino-N-(o-carbamoylphenyl)benzamide): Preparation and use as a synthetic precursor for quinazolino[1,2,3]benzotriazinones

Eddy¹,

Vaughan²,

Stevens³

1978

Can. J. Chem.

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“…Features (d) and (e), however, might appear to contradict the intermolecular interpretation but this discrepancy is only apparent : the failure to trap CH30-CO-NH2 in the rearrangement of (1) can be reasonably explained by the much lower reactivity of RO-CO-N H2 with respect to RO-CO-NH-(the reaction between C~HS-CO-CHO and C2H50-CO-NH2 requires several hours at reflux). On the other hand, trapping of the substituted glyoxal by (11) to give a mixture of (11) and (XV) as in Scheme 10, which even though at first sight might appear to restrict the significance of the crossover experiment (a), still indirectly supports the intermolecular interpretation of this rearrangement since Scheme 10 implies the presence of free glyoxal which can only be formed during an intermolecular process.…”

Section: Resultsmentioning

confidence: 86%

“…Reaction between (11) and (XVI), and (XV) and (XVII) in the presence of TEA. Solutions of (11) (0.056 g, 0.25 mmol) and (XVI) (0.073 g, 0.025 mmol), or of (XV) (0.25 g, 0.86 mmol) and ( X V I I ) (0.18 g, 0.83 mmol) in dry CH2C12 treated with TEA as previously described and submitted to h.p.1.c.…”

Section: -Methyl-3-hydroxy-23-dihydro-i H-isoindol-1 -One (Xiii)mentioning

confidence: 99%

Reactivity of N-phenacyloxycarbamates and related systems in the presence of bases: study of a new [1,2] anionic rearrangement

Consonni¹,

Favara²,

Omodei-Salè³

et al. 1983

J. Chem. Soc., Perkin Trans. 2

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N-Phenacyloxycarbamates and other systems containing a CH,-0-N= framework, in the presence of bases, undergo a CH,-0-N= --+ CH(0H)-N= rearrangement. The mechanism of this reaction has been studied kinetically and through crossover and capture experiments. The bulk of the data favours an intermolecular ionic mechanism which occurs by removal of a proton from the methylene group in the rate-determining step, followed by interaction between a glyoxal molecule and a carbamate anion in the fast step of the reaction.* a-Chloro-a-phenylacetophenone.

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“…[223] N,N-Dialkylhydroxylamines have also attracted growing interest as pharmacophores or toxophores in drug and agrochemistry. [224][225][226][227][228] In addition, the oxidative metabolism of secondary amines produces N,N-dialkylhydroxylamines. [229][230][231][232] Methods for N,N-dialkylhydroxylamine preparation have been reviewed up to 1990 (see Houben-Weyl, Vol.…”

Section: T-bumentioning

confidence: 99%