1503-92-0Relevant academic research and scientific papers
Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides
Du, Yuanbo,Feng, Lei,Gao, Hongyin,Guo, Lirong,Lu, Haifeng,Xi, Zhenguo
supporting information, (2021/05/19)
A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.
Cascade Approach to Highly Functionalized Biaryls by a Nucleophilic Aromatic Substitution with Arylhydroxylamines
Guo, Lirong,Liu, Fengting,Wang, Liying,Yuan, Hairui,Feng, Lei,Kürti, László,Gao, Hongyin
supporting information, p. 2894 - 2898 (2019/04/25)
A transition-metal free synthesis of highly functionalized 2-hydroxy-2′-amino-1,1′-biaryls from N-arylhydroxylamines has been developed. This operationally simple and readily scalable approach relies on a cascade of reactions that initially generates transient N,O-diarylhydroxylamines, via direct O-arylation, which then undergo rapid [3,3]-sigmatropic rearrangement and subsequent rearomatization to form NOBIN-type products. These structurally diverse functionalized biaryls are obtained under mild conditions in good to excellent isolated yields.
Interrupted fischer-indole intermediates via oxyarylation of alkenyl boronic acids
Wang, Heng-Yen,Anderson, Laura L.
supporting information, p. 3362 - 3365 (2013/07/26)
The oxyarylation of alkenyl boronic acids with N-arylbenzhydroxamic acids has been achieved under both copper-mediated and copper-catalyzed conditions to provide access to interrupted Fischer-indole intermediates. This transformation is believed to proceed through a copper-promoted C-O bond forming event followed by a [3,3] rearrangement. The scope of the method is described and mechanistic experiments are discussed.
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
