Department of Chemistry, Zhejiang Sci-Tech University, Xiasha Campus, Hangzhou, 310018, P. R. China.
School of Materials Science and Engineering, Zhejiang Sci-Tech University, Hangzhou, 310018, P. R. China.
Chemistry. 2020 Nov 17;26(64):14565-14569. doi: 10.1002/chem.202003003. Epub 2020 Oct 14.
A new procedure on palladium-catalyzed carbonylative cyclization of N-(2-pyridyl)sulfonyl (N-SO Py)-2-iodoanilines with terminal alkenes has been developed for the rapid construction of dihydroquinolin-4(1H)-one scaffolds. Enabled by the chelating group and using benzene-1,3,5-triyl triformate (TFBen) as the CO source, both aromatic and aliphatic alkenes were smoothly transformed into the corresponding 2,3-dihydroquinolin-4(1H)-ones in good yields with excellent regioselectivities. Notably, the reaction of aromatic alkenes produces 2-aryl-2,3-dihydroquinolin-4(1H)-ones, while 3-alkyl-2,3-dihydroquinolin-4(1H)-ones were obtained when aliphatic alkenes were used. This protocol has been applied in the synthesis of antitumor agent A as well.
一种新的钯催化羰基环化反应，用于 N-(2-吡啶基)磺酰基 (N-SO Py)-2-碘代苯胺与末端烯烃的快速构建二氢喹啉-4(1H)-酮骨架。在螯合基团的作用下，使用三苯甲酸三乙酯 (TFBen) 作为 CO 源，芳香族和脂肪族烯烃都能以良好的收率和优异的区域选择性顺利转化为相应的 2,3-二氢喹啉-4(1H)-酮。值得注意的是，芳香族烯烃的反应生成 2-芳基-2,3-二氢喹啉-4(1H)-酮，而脂肪族烯烃则生成 3-烷基-2,3-二氢喹啉-4(1H)-酮。该方法也已应用于抗肿瘤药物 A 的合成。
Zotero 插件