1315571-17-5Relevant 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
, p. 2094 - 2097 (2015)
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.
Copper-catalysed intramolecular O-arylation: A simple and efficient method for benzoxazole synthesis
Wu, Fengtian,Zhang, Jie,Wei, Qianbing,Liu, Ping,Xie, Jianwei,Jiang, Haojie,Dai, Bin
supporting information, p. 9696 - 9701 (2015/02/19)
A wide range of 2-substituted benzoxazoles can be efficiently synthesized from N-(2-iodo-/bromo-phenyl)benzamides, and even the less reactive N-(2-chlorophenyl)benzamides, via Cu-catalysed intramolecular coupling cyclization reactions using methyl 2-methoxybenzoate as the ligand under mild reaction conditions. In addition, the benzoxazoles can be easily prepared from the primary amides coupling with o-dihalobenzenes in a single step. This journal is
Mesoporous poly(melamine-formaldehyde): A green and recyclable heterogeneous organocatalyst for the synthesis of benzoxazoles and benzothiazoles using dioxygen as oxidant
Yang, Daoshan,Liu, Peng,Zhang, Ning,Wei, Wei,Yue, Mingbo,You, Jinmao,Wang, Hua
, p. 3434 - 3439 (2015/04/16)
A simple, highly efficient, and sustainable strategy for the synthesis of benzoxazole and benzothiazole derivatives was developed by using inexpensive, green, readily available, and recyclable mesoporous poly(melamine-formaldehyde) as a green, heterogeneous organocatalyst. The corresponding substituted benzoxazoles and benzothiazoles were obtained in good to excellent yields by aerobic oxidation of o-substituted aminobenzenes with various aldehydes under dioxygen atmosphere. The catalyst can be completely recovered through simple filtration to be reused more than six times without significant loss of catalytic activity.