Liu Jin-Yi, Zhuang Shi-Yi, Tang Yong-Xing, Chen Xiang-Long, Zhou You, Wu Yan-Dong, Zheng Kai-Lu, Wu An-Xin
National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
Guangdong Provincial Key Laboratory of Research and Development of Natural Drugs, The First Dongguan Affiliated Hospital, Guangdong Medical University, Dongguan 523808, P. R. China.
J Org Chem. 2023 Aug 18;88(16):12000-12012. doi: 10.1021/acs.joc.3c01327. Epub 2023 Aug 4.
An I-DMSO-mediated multicomponent [3+1+2] cascade annulation reaction using aryl methyl ketones, enaminones, and benzo[]isoxazol-3-amine as substrates has been developed. This metal-free reaction involved the transannulation of benzo[]isoxazol-3-amines with the formation of two C-N bonds and a C-C bond in one pot. Notably, a pyrimidine ring with a 1,4-dicarbonyl scaffold could efficiently transform into a pyrimido[4,5-]pyridazine skeleton. The phenolic hydroxyl group of the target product could undergo further modification with pharmaceuticals, demonstrating the utility of this method.
已开发出一种以芳基甲基酮、烯胺酮和苯并[ ]异恶唑-3-胺为底物的I-DMSO介导的多组分[3+1+2]串联环化反应。这种无金属反应涉及苯并[ ]异恶唑-3-胺的跨环化反应，能在一锅反应中形成两个C-N键和一个C-C键。值得注意的是，具有1,4-二羰基骨架的嘧啶环可有效转化为嘧啶并[4,5-]哒嗪骨架。目标产物的酚羟基可与药物进行进一步修饰，证明了该方法的实用性。
