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Ce(OTf)3-Catalyzed Multicomponent Reaction of Alkynyl Carboxylic Acids, tert-Butyl Isocyanide, and Azides for the Assembly of Triazole-Oxazole Derivatives.
ACS Combinatorial Science ( IF 3.903 ) Pub Date : 2020-04-20 , DOI: 10.1021/acscombsci.0c00012
Ming Cao 1 , Yi-Lin Fang 2 , Ying-Chun Wang 1 , Xiao-Juan Xu 1 , Zhi-Wei Xi 1 , Shi Tang 1
Affiliation  

Cerium(III) triflate-catalyzed multicomponent reactions between alkynyl carboxylic acids, tert-butyl isocyanide, and organic azides have been developed. In the presence of Ce(OTf)3 (10 mol %), the cascade reaction of one molecule of alkynyl carboxylic acid with three molecules of tert-butyl isocyanides proceeds chemoselectively and regioselectively via a triple and ordered isocyanide insertion process at room temperature, and then the cesium-catalyzed [3 + 2] cycloaddtion reaction between the resulted alkynyl oxazole and organic azides was further initiated by the temperature elevation (100 °C), thereby leading to multisubstituted triazole-oxazole derivatives in practical, time-saving, one-pot operations. Furthermore, some of the synthesized target compounds showed potential anticancer activities against MGC803 (human gastric cancer cell) with IC50 values below 20 μmol L-1.

中文翻译:

Ce(OTf)3催化的炔基羧酸,叔丁基异氰酸酯和叠氮化物的多组分反应,用于组装三唑-恶唑衍生物。

已经开发了炔丙基羧酸,叔丁基异氰酸酯和有机叠氮化物之间的三氟甲磺酸铈(III)催化的多组分反应。在Ce(OTf)3(10 mol%)的存在下,一分子炔基羧酸与三分子叔丁基异氰酸酯的级联反应在室温下通过三重和有序异氰酸酯插入过程进行化学选择性和区域选择性的反应,然后然后通过升高温度(100°C)进一步引发所得炔基恶唑与有机叠氮化物之间的铯催化的[3 + 2]环加成反应,从而制得实用,省时,单效的多取代三唑-恶唑衍生物。锅操作。此外,
更新日期:2020-04-10
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