1620817-48-2Relevant academic research and scientific papers
Cesium Fluoride and Copper-Catalyzed One-Pot Synthesis of Benzoxazoles via a Site-Selective Amide C?N Bond Cleavage
Luo, Zhongfeng,Wu, Hongxiang,Li, Yue,Chen, Yuwen,Nie, Jingyi,Lu, Siqi,Zhu, Yulin,Zeng, Zhuo
, p. 4117 - 4125 (2019/08/01)
We report herein a two-step one-pot strategy for the synthesis of benzoxazoles from amides by using cesium fluoride/copper as catalysts. This approach involves the in situ generation of acyl fluorides from the corresponding amides, and the acyl fluorides undergo transamidation and cyclization to give benzoxazoles in good yields. In this work, the amide C?N bonds are activated by CsF to form the acyl fluoride intermediates, which further react with o-bromoanilines to efficiently yield benzoxazoles. Notably, this methodology demonstrates a broad substrate scope, as primary/secondary benzamides are well tolerated, and this process might facilitate the development of one-pot transformations of amides. (Figure presented.).
Organocatalytic syntheses of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation
Alla, Santhosh Kumar,Sadhu, Pradeep,Punniyamurthy, Tharmalingam
, p. 7502 - 7511 (2014/09/16)
An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.
