27687-56-5Relevant academic research and scientific papers
N-heterocyclic-carbene-catalyzed one-pot synthesis of hydroxamic esters
Song, Xiaoxiao,Ni, Qijian,Grossmann, Andre,Enders, Dieter
supporting information, p. 2965 - 2969 (2014/01/06)
The honey pot: The NHC-catalyzed reaction between nitrosobenzenes, aromatic/aliphatic aldehydes, and enals proceeded through an aza-benzoin-type reaction and an internal redox esterification to afford hydroxamic esters in good yields. Copyright
The thiamine-dependent enzyme of the vitamin K biosynthesis catalyzes reductive C-N bond ligation between nitroarenes and α-ketoacids
Chen, Min Jiao,Jiang, Ming,Guo, Zhi Hong
, p. 312 - 320 (2013/07/26)
The thiamine-dependent enzyme (1R, 2S, 5S, 6S)-2-succinyl-5-enolpyruvyl-6- hydroxyl-3-cyclohexene-1-carboxylate (SEPHCHC) synthase, also known as MenD, catalyzes a Stetter-like reaction in the biosynthesis of vitamin K. It is found to catalyze a novel reductive C-N bond ligation reaction between nitroarenes and α-ketoacids to form N-hydroxamates. This reaction likely proceeds through an enzyme-mediated, slow two-electron reduction of the nitroalkanes to form a nitroso intermediate, which serves as the electrophilic acceptor of the ketoacid-derived acyl anion. The involvement of the nitroso intermediate is supported by the fact that similar N-hydroxamates are readily formed at a much higher rate when nitroso compounds replace the nitro substrates in the chemoenzymatic reactions. These results demonstrate that the thiamine-dependent enzyme is able to catalyze novel, nonnative reactions that may find new chemoenzymatic applications.
N-Arylhydroxamic Acids: Reaction of Nitroso Aromatics with α-Oxo Acids
Sakamoto, Yasuko,Yoshioka, Tadao,Uematsu, Takayoshi
, p. 4449 - 4453 (2007/10/02)
A practical and high-yielding route to N-arylhydroxamic acids from nitroso aromatics and α-oxo acids 1a-d is desctibed.In aqueous and acetic acid containing media, the reactions exhibit second-order reaction kinetics overall.In the aqueous medium, the rate constant (kobsd) for N-phenylacetohydroxamic acid (8b) formation increased with increasing +>, though there were some side pathways involving azoxybenzene formation.In general, kobsd for the reaction in the acetic acid containing medium was about one-tenth of that in HCl at pH 0.6.On a preparative scale, acetic acid is better than HCl, in that both reactants showed sufficient solubilities in acetic acid for a high reaction velocity and no side reaction was detected.With this method, the proximate carcinogens, N-(4-biphenylyl)acetohydroxamic acid (12b) and N-(2-fluorenyl)acetohydroxamic acid (13b), could be easily prepared.Under both conditions, the order of kobsd for the reactions of nitrosobenzene (2) with α-oxo acids 1a-d was glyoxylic (1a) > pyruvic (1b) 2-oxobutyric (1c) > benzoylformic (1d) acid.For the reactions of substituted nitrosobenzenes 3-6 with pyruvic acid (1b), the order of kobsd was p-phenyl (6) > unsubstituted (2) > p-chloro (5) > m-chloro (4) >> o-chloro (3) nitrosobenzene.The negative Hammett reaction constant value obtained indicates that an electron-donating substituent is preferable for the reaction.The reaction mechanism and other factors affecting N-arylhydroxamic acid formation are also descussed.
Quantitative Treatment of Reaction Rates in Functional Micelles and Comicelles
Bunton, Clifford A.,Hamed, Fareed H.,Romsted, Laurence S.
, p. 2103 - 2108 (2007/10/02)
Comicelles of dodecyldimethylammonium bromide (5) or N-phenylmyristohydroxamic acid (6) with cetyltrimethylammonium bromide (CTABr) are good dephosphorylating agents toward p-nitrophenyldiphenyl phosphate (p-NPDPP) at high p
