152993-82-3Relevant articles and documents
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.
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.
