55045-05-1Relevant academic research and scientific papers
Aromatic amine compound, EphB4 kinase inhibitor and its derivatives, and preparation methods thereof
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Paragraph 0185-0187, (2019/11/04)
The invention provides an aromatic amine compound, an EphB4 kinase inhibitor and its derivatives, and preparation methods thereof. Aryl boronic acid or aryl boronate and O-benzoyl hydroxylamine compounds which are used as starting raw materials are stirred and reacted in an organic solvent at 30-100 DEG C in an air atmosphere under the action of a palladium catalyst, a norbornene derivative and analkali, and separation and purification are carried out after the reaction in order to obtain the aromatic amine compound. The method has the advantages of inexpensive and readily available raw materials, no halide ion residual after the completion of the reaction, and mild reaction conditions. The invention also provides the method for synthesizing the EphB4 kinase inhibitor and its derivatives.The EphB4 kinase inhibitor and its derivatives can be synthesized from the synthesized 3,5-diminated halogenobenzene or halogenoid benzene only through a simple step.
Redox-neutral: Ortho -C-H amination of pinacol arylborates via palladium(ii)/norbornene catalysis for aniline synthesis
Chen, Shuqing,Wang, Peng,Cheng, Hong-Gang,Yang, Chihui,Zhou, Qianghui
, p. 8384 - 8389 (2019/09/30)
A palladium(ii)/norbornene cooperative catalysis enabled redox-neutral ortho-C-H amination of pinacol aryl- or heteroarylborates for the synthesis of structurally diverse anilines is reported. This method is scalable, robust (tolerance of air and moisture), phosphine ligand-free, and compatible with a wide range of functionalities. These practical features make this reaction amenable for industry. A plethora of synthetically very useful halogenated anilines, which often cannot be prepared via other transition-metal-catalyzed aminations, are readily produced using this method. Particularly, the orthogonal reactivity between pinacol arylborates and aryl iodides is demonstrated. Preliminary deuterium-labeling studies reveal a redox-neutral ipso-protonation mechanism of this process, which will surely inspire the future development of this field. Overall, the exceptionally broad scope (47 examples) and reliability of this procedure, together with the wide availability of pinacol arylborates, make this chemistry a valuable addition to the existing methods for aniline synthesis.
Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite
Kaga, Atsushi,Hayashi, Hirohito,Hakamata, Hiroyuki,Oi, Miku,Uchiyama, Masanobu,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 11807 - 11811 (2017/09/20)
A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.
Ni0-catalyzed direct animation of anisoles involving the cleavage of carbon-oxygen bonds
Tobisu, Mamoru,Shimasaki, Toshiaki,Chatani, Naoto
supporting information; experimental part, p. 710 - 711 (2011/04/22)
Ni0-catalyzed cross-coupling of aryl methyl ethers with amines is described. The use of an N-heterocyclic carbene as a ligand and NaOt-Bu as a base promotes the amination of anisole derivatives via the cleavage of normally unreactive aryl carbo
