155249-15-3Relevant academic research and scientific papers
Synthesis of O- tert-Butyl- N,N-disubstituted Hydroxylamines by N-O Bond Formation
Hill, Jarvis,Crich, David
, p. 6396 - 6400 (2021)
The reaction of magnesium amides with tert-butyl 2,6-dimethyl perbenzoate in tetrahydrofuran at 0 °C provides a method for the synthesis O-tert-butyl-N,N-disubstituted hydroxylamines by direct N-O bond formation with a broad functional group tolerance. Less sterically hindered magnesium amides require ortho,ortho-disubstitution on the perester electrophile component, whereas sterically encumbered magnesium amides perform comparably with either tert-butyl perbenzoate or tert-butyl 2,6-dimethyl perbenzoate. A reaction mechanism is presented to account for the observed reactivity.
DIVERSITY-ORIENTED SYNTHESIS OF N,N,O-TRISUBSTITUTED HYDROXYLAMINES FROM ALCOHOLS AND AMINES BY N-O BOND FORMATION
-
Page/Page column 0295; 0304; 0306, (2021/11/26)
In one aspect, the disclosure relates to a method for the direct synthesis of complex N,N,O-trisubstituted hydroxylamines by N—O bond formation. In another aspect, the method can successfully be employed using a wide variety of commercially available alcohols and secondary amines and enables the construction of large fragment-based libraries of trisubstituted hydroxylamines for drug discovery purposes. Also disclosed are N,N,O-trisubstituted hydroxylamines having low basicity, high stability at ambient temperatures, and an inherent lack of reactivity towards acetylating and sulfonylating enzymes that confer mutagenicity on less-substituted hydroxylamines.
