16237-47-1Relevant academic research and scientific papers
Chemoselective amide formation using O-(4-nitrophenyl)hydroxylamines and pyruvic acid derivatives
Kumar, Sonali,Sharma, Rashi,Garcia, Megan,Kamel, Joseph,McCarthy, Caroline,Muth, Aaron,Phanstiel, Otto
, p. 10835 - 10845 (2013/02/23)
A series of O-(4-nitrophenyl)hydroxylamines were synthesized from their respective oximes using a pulsed addition of excess NaBH3CN at pH 3 in 65a-75% yield. Steric hindrance near the oxime functional group played a key role in both the ease by which the oxime could be reduced and the subsequent reactivity of the respective hydroxylamine. Reaction of the respective hydroxylamines with pyruvic acid derivatives generated the desired amides in good yields. A comparison of phenethylamine systems bearing different leaving groups revealed significant differences in the rates of these systems and suggested that the leaving group ability of the Na-OR substituent plays an important role in determining their reactivity with pyruvic acid. Competition experiments (in 68% DMSO/phosphate buffered saline) using 1 equiv of N-phenethyl-O-(4-nitrophenyl)hydroxylamine and 2 equiv of pyruvic acid in the presence of other nucleophiles such as glycine, cysteine, phenol, hexanoic acid, and lysine demonstrated that significant chemoselectivity is present in this reaction. The results suggest that this chemoselective reaction can occur in the presence of excess α-amino acids, phenols, acids, thiols, and amines.
Polymer-supported copper complex for the direct synthesis of O-aryloxime ethers via cross-coupling of oximes and arylboronic acids
Wang, Liang,Huang, Chengyan,Cai, Chun
experimental part, p. 532 - 536 (2010/07/16)
L-proline functionalized chloroacetylated polystyrene supported copper (II) complex was prepared and found to be effective for the cross-coupling reaction between aromatic oximes and arylboronic acids under mild conditions. Only catalytic amount of cataly
