62458-12-2Relevant articles and documents
Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazolesviaredox condensation ofo-nitrophenols with acetophenones and methylquinolines
Ngo, Quoc Anh,Nguyen, Le Anh,Nguyen, Thanh Binh,Nguyen, Thi Thu Tram
supporting information, p. 6015 - 6020 (2021/07/21)
An Fe/S catalyst generatedin situfrom FeCl2·4H2O and elemental sulfur S8in the presence of a tertiary amine as a base was found to catalyze efficiently a 6e?redox condensation ofo-nitrophenols with acetophenones and methylquinolines. The condensed products 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles were obtained in reasonable yields with water as the only byproduct at a temperature as low as 80 °C.
Break-and-Build Strategy for the Synthesis of 2-Benzoylbenzoxazoles from o-Aminophenols and Acetophenones
Nguyen, Le Anh,Ngo, Quoc Anh,Retailleau, Pascal,Nguyen, Thanh Binh
supporting information, p. 2098 - 2103 (2021/03/15)
Although compounds with a 2-benzoylbenzoxazole motif are biologically relevant, there are only a few methods for synthesizing them, most of which relied on multistep process or required substrates bearing activating groups. Herein, we report an efficient method for the synthesis of such compounds by direct reactions of o-aminophenols with acetophenones promoted by sulfur in DMSO. The reaction was found to proceed via a Willgerodt rearrangement-type benzoxazolation of acetophenones followed by a benzylic oxidation to reinstall the carbonyl function. This method has a broad substrate scope and good tolerance for sensitive functional groups. (Figure presented.).
Synthesis of 2-Keto(hetero)aryl Benzox(thio)azoles through Base Promoted Cyclization of 2-Amino(thio)phenols with α,α-Dihaloketones
Jiang, Jun,Zou, Huaxu,Dong, Qizhi,Wang, Ruijia,Lu, Linghui,Zhu, Yonggang,He, Weimin
, p. 51 - 56 (2016/01/15)
An interesting base-promoted protocol for the synthesis of 2-keto(hetero)aryl benzox(thi)azoles has been developed. Starting from commercially available 2-amino(thio)phenols and α,α-dihaloketones, moderate to good yields of the corresponding heterocycles can be achieved. Notably, only EtNH2 was required as the promoter here, and the reaction can be easily performed on a large scale.