通过铑催化芳族酰胺与N-乙烯基邻苯二甲酰亚胺的烷基化反应合成3,4-二氢异喹啉-1(2H)-酮
A Synthesis of 3,4-Dihydroisoquinolin-1(2H)-one via the Rhodium-Catalyzed Alkylation of Aromatic Amides with N-Vinylphthalimide.
作者信息
He Qiyuan, Chatani Naoto
机构信息
Department of Applied Chemistry, Faculty of Engineering , Osaka University , Suita , Osaka 565-0871 , Japan.
出版信息
J Org Chem. 2018 Nov 2;83(21):13587-13594. doi: 10.1021/acs.joc.8b02249. Epub 2018 Oct 17.
The alkylation of C-H bonds with N-vinylphthalimide by a rhodium-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety as the directing group is reported. N-Vinylphthalimide functions as a 2-aminoethylating reagent. The resulting alkylated products can be converted into 3,4-dihydroisoquinolin-1(2H)-one derivatives in a one-pot transformation. Deuterium-labeling experiments suggest that the reaction proceeds through a carbene mechanism.
报道了通过铑催化的、以含8-氨基喹啉部分作为导向基团的芳香酰胺反应，实现C-H键与N-乙烯基邻苯二甲酰亚胺的烷基化反应。N-乙烯基邻苯二甲酰亚胺作为一种2-氨基乙基化试剂。所得的烷基化产物可通过一锅法转化为3,4-二氢异喹啉-1(2H)-酮衍生物。氘标记实验表明该反应通过卡宾机理进行。
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