School of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala 147001, India.
J Org Chem. 2022 Aug 19;87(16):10673-10683. doi: 10.1021/acs.joc.2c00872. Epub 2022 Aug 5.
The quinazolinone template offers an exciting potential for transforming molecules into useful bioactivity. Herein, we report the first regioselective C-5 alkenylation of quinazolinone-coumarin conjugates via ruthenium(II) catalyst using amide as a weak directing group. This methodology permits excellent regioselectivity, extensive substrate tolerance, and mild reaction conditions. In addition, it generates interesting fluorophores that show positive solvatochromism in the range from 404 nm (toluene) to 541 nm (methanol).
喹唑啉酮模板为将分子转化为有用的生物活性提供了令人兴奋的潜力。在此，我们报告了首例通过钌（II）催化剂使用酰胺作为弱导向基团对喹唑啉酮-香豆素缀合物进行区域选择性 C-5 烯基化反应。该方法具有优异的区域选择性、广泛的底物耐受性和温和的反应条件。此外，它还生成了有趣的荧光团，在 404nm（甲苯）到 541nm（甲醇）的范围内表现出正溶剂化变色。
