152993-82-3Relevant academic research and scientific papers
Access to 2-(het)aryl and 2-styryl benzoxazoles via palladium-catalyzed aminocarbonylation of aryl and vinyl bromides
Neumann, Karoline T.,Lindhardt, Anders T.,Bang-Andersen, Benny,Skrydstrup, Troels
supporting information, p. 2094 - 2097 (2015/05/13)
A sequential one-pot procedure for the synthesis of either 2-(hetero)aryl or 2-styryl benzoxazoles is reported, starting from aryl and vinyl bromides, respectively, involving an initial aminocarbonylation with 2-aminophenols as nucleophiles followed by an acid mediated ring closure to generate the heterocycle. The methodology displays a broad substrate scope in moderate to excellent yields and can be exploited for 13C-isotope labeling. Finally, this carbonylative protocol was applied to the synthesis of a potential Alzheimer's plaque binder and a selective PPAR antagonist including site-specific labeling with 13C-carbon monoxide.
Ruthenium-catalyzed synthesis of benzoxazoles using acceptorless dehydrogenative coupling reaction of primary alcohols with 2-aminophenol under heterogeneous conditions
Khalafi-Nezhad, Ali,Panahi, Farhad
, p. 1686 - 1692 (2014/06/24)
An efficient ruthenium-catalyzed acceptorless dehydrogenative coupling reaction of primary alcohols with 2-aminophenol for one-pot synthesis of benzoxazoles is introduced. The phosphine-functionalized magnetic nanoparticles (PFMNPs; Fe3O4@SiO2@PPh2) as a magnetic recyclable phosphorus ligand in the presence of Ru2Cl 4(CO)6 was found to be an efficient heterogeneous catalytic system for promotion of the designed protocol. The reaction was carried out efficiently with a variety of substrates to give the corresponding products in moderate to good yields.
Transition-metal free 2-arylbenzoxazole formation from aryl amides and cyclohexanones
Cao, Xiangxiang,Cheng, Xiufang,Bai, Yang,Liu, Saiwen,Deng, Guo-Jun
supporting information, p. 4644 - 4648 (2015/02/19)
A transition-metal-free method for the synthesis of 2-arylbenzoxazoles from readily available cyclohexanones and benzamides is described. The combined use of KI, p-TsOH and DMSO significantly improved the reaction yields. Non-aromatic cyclohexanones were smoothly dehydrogenated and acted as the aryl source using oxygen as the oxidant.
Nickel-catalyzed decarboxylative arylation of heteroarenes through sp2 C-H functionalization
Yang, Ke,Wang, Peng,Zhang, Cheng,Kadi, Adnan A.,Fun, Hoong-Kun,Zhang, Yan,Lu, Hongjian
supporting information, p. 7586 - 7589 (2015/04/22)
The direct decarboxylative arylation of hetereoarenes with benzoic acids through a nickel-catalyzed sp2 C-H functionalization process was developed. This process provides the first examples of decarboxylative cross-coupling reactions with aroma
