三氟甲基化/全氟烷基化腙酰氯与氟代硝基烯烃的区域选择性[3 + 2]环加成反应：制备 3-三氟甲基-5-氟吡唑的简便方法。
Regioselective [3 + 2] cycloaddition of di/trifluoromethylated hydrazonoyl chlorides with fluorinated nitroalkenes: a facile access to 3-di/trifluoroalkyl-5-fluoropyrazoles.
机构信息
Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Frontiers Science Center for Synthetic Biology (Ministry of Education), and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China.
Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, P. R. of China.
出版信息
Org Biomol Chem. 2023 Jun 21;21(24):5040-5045. doi: 10.1039/d3ob00644a.
Herein we describe the base-mediated [3 + 2] cycloaddition reaction of di/trifluoromethylated hydrazonoyl chlorides with fluorinated nitroalkenes. The reaction protocol provides a direct and facile strategy for the dual incorporation of a fluorine atom and fluoroalkyl group into pyrazole cores, thus allowing rapid access to a wide variety of densely functionalized 3-di/trifluoroalkyl-5-fluoropyrazoles in generally high yields with excellent regioselectivities. Furthermore, several drug-like 3-di/trifluoroalkyl-5-fluoropyrazoles have been synthesized, demonstrating potent inhibitory activities against cyclooxygenase 2 (COX-2).
在此，我们描述了二/三氟甲基化腙酰氯与氟化硝基烯烃的碱介导的 [3 + 2] 环加成反应。该反应方案提供了一种将氟原子和氟烷基双官能团直接导入吡唑核的简便方法，从而能够快速获得广泛的各种高度官能化的 3-二/三氟烷基-5-氟吡唑，通常具有优异的区域选择性和高收率。此外，还合成了几种类似药物的 3-二/三氟烷基-5-氟吡唑，它们对环氧化酶 2（COX-2）表现出很强的抑制活性。
Zotero 插件