Oxaziridine-Mediated Amination of Primary Amines:  Scope and Application to a One-Pot Pyrazole Synthesis

Armstrong, Alan; Jones, Lyn H.; Knight, Jamie D.; Kelsey, Richard D.

doi:10.1021/ol0474507

Cited by 91 publications

(64 citation statements)

References 13 publications

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“…Additionally, the Armstrong group reported a route to the key aza-Wittig reagent 15 that avoids the use of the potentially hazardous Boc azide (Scheme 5). 37 …”

Section: Synthesis and Physical Properties Of Oxaziridinesmentioning

confidence: 99%

Advances in the Chemistry of Oxaziridines

2014

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“…Additionally, the Armstrong group reported a route to the key aza-Wittig reagent 15 that avoids the use of the potentially hazardous Boc azide (Scheme 5). 37 …”

Section: Synthesis and Physical Properties Of Oxaziridinesmentioning

confidence: 99%

Advances in the Chemistry of Oxaziridines

2014

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“…Synthetic TXPTS aza-ylide was obtained through the amidation of TXPTS using hydroxylamine O-sulfonic acid in water. 30 Melting point measurements are uncorrected. NMR spectra were obtained on a 400 MHz FT-NMR spectrometer.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Curtailing the Hydroxylaminobarbituric Acid–Hydantoin Rearrangement To Favor HNO Generation

et al. 2015

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Due to its inherent reactivity, HNO must be generated in situ through the use of donor compounds. One of the primary strategies for the development of new HNO donors has been modifying hydroxylamines with good leaving groups. A recent example of this strategy is the (hydroxylamino)barbituric acid (HABA) class of HNO donors. In this case, however, an undesired intramolecular rearrangement pathway to the corresponding hydantoin derivative competes with HNO formation, particularly in the absence of chemical traps for HNO. This competitive non-HNO-producing pathway has restricted the development of the HABA class to examples with fast HNO release profiles at physiological pH and temperature (t(1/2) < 1 min). Herein, the factors that favor the rearrangement pathway have been examined and two independent strategies that protect against rearrangement to favor HNO generation have been developed. The timecourse and stoichiometry for the in vitro conversion of these compounds to HNO (trapped as a phosphine aza-ylide) and the corresponding barbituric acid (BA) byproduct have been determined by (1)H NMR spectroscopy under physiologically relevant conditions. These results confirm the successful extension of the HABA class of pure HNO donors with half-lives at pH 7.4, 37 °C ranging from 19 to 107 min.

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“…N-Ethyl-tyramine (9), 56 3-methyl-3-butenyl acetate (60), 57 and 2-methallyl acetate (61) 57 were prepared according to literature.…”

Section: Scheme 5 Oxidation Of Phenylazocarboxylatesmentioning

confidence: 99%

Nucleophilic Substitutions and Radical Reactions of Phenylazocarboxylates

2012

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tert-Butyl phenylazocarboxylates are versatile building blocks for synthetic organic chemistry. Nucleophilic substitutions of the benzene ring proceed with aromatic amines and alcohols under mild conditions. The attack of aliphatic amines may be directed to the aromatic core as well as to the carbonyl unit leading to azocarboxamides. The benzene ring can further be modified through radical reactions, in which the tert-butyloxycarbonylazo group enables the generation of aryl radicals at either elevated temperatures or under acidic conditions. Radical reactions include oxygenation, halogenation, carbohalogenation, carbohydroxylation, and aryl-aryl coupling.

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Oxaziridine-Mediated Amination of Primary Amines: Scope and Application to a One-Pot Pyrazole Synthesis

Cited by 91 publications

References 13 publications

Advances in the Chemistry of Oxaziridines

Advances in the Chemistry of Oxaziridines

Curtailing the Hydroxylaminobarbituric Acid–Hydantoin Rearrangement To Favor HNO Generation

Nucleophilic Substitutions and Radical Reactions of Phenylazocarboxylates

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