O-2,4-Dinitrophenylhydroxylamine

Development of a Practical Synthesis of a p38 Kinase Inhibitor via a Safe and Robust Amination

“…Amination of heterocycles has been reported using a variety of hydroxylamine-based electrophilic NH 2 + equivalents, such as O -acyl, O -alkyl, O -sulfonyl, O -nitrophenyl, and O -diarylphosphinyl derivatives. Unfortunately, most of these reagents are not commercially available, or they are thermally instable.…”

Amination of Heterocyclic Compounds with O-Benzoylhydroxylamine Derivatives

“…The amination of nitrogen and carbon nucleophiles is an attractive tool for synthetic and medicinal chemists and can provide easy access to a variety of useful substances. Numerous NH 2 -transfer agents have been previously described in the literature, including a variety of hydroxylamine-based compounds, such as the O -acyl, O -alkyl, O -sulfonyl, 1a, O -nitrophenyl, and O -diarylphosphinyl 6 derivatives. However, due to their limited availability, ,6a, stability, ,2c,4a as well as the safety concerns around their handling, 5a, the latter class of compounds has seen limited utility in large scale processes.…”

“…Numerous NH 2 -transfer agents have been previously described in the literature, including a variety of hydroxylamine-based compounds, such as the O -acyl, O -alkyl, O -sulfonyl, 1a, O -nitrophenyl, and O -diarylphosphinyl 6 derivatives. However, due to their limited availability, ,6a, stability, ,2c,4a as well as the safety concerns around their handling, 5a, the latter class of compounds has seen limited utility in large scale processes. Therefore, seeking and developing safe, convenient, and efficient reagents and processes for the direct amination of carbon and nitrogen nucleophiles continues to be an area of interest in organic synthesis. 2a,5a,6a, …”

“…However, due to their limited availability, ,6a, stability, ,2c,4a as well as the safety concerns around their handling, 5a, the latter class of compounds has seen limited utility in large scale processes. Therefore, seeking and developing safe, convenient, and efficient reagents and processes for the direct amination of carbon and nitrogen nucleophiles continues to be an area of interest in organic synthesis. 2a,5a,6a, …”

Comparison of Electrophilic Amination Reagents for N-Amination of 2-Oxazolidinones and Application to Synthesis of Chiral Hydrazones

“…An attractive possibility for synthesis of N -acylhydrazones is the direct transfer of the unprotected amino group. A number of hydroxylamine derivatives (see Chart ) are competent electrophilic NH 2 + equivalents that have been shown to transfer the amino group to various oxygen or nitrogen nucleophiles, including deprotonated amides 14a…”