醋酸铜引发的丙二酸连接的酰基肟与吲哚、吲哚 -2-醇和吲哚 -2-甲酰胺的串联反应。
Cu(OAc)-Triggered Cascade Reaction of Malonate-Tethered Acyl Oximes with Indoles, Indole-2-alcohols, and Indole-2-carboxamides.
作者信息
Mao Peng-Fei, Zhou Li-Jin, Zheng An-Qi, Miao Chun-Bao, Yang Hai-Tao
机构信息
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering , Changzhou University , 1 Gehu Road , Changzhou , Jiangsu 213164 , China.
出版信息
Org Lett. 2019 May 3;21(9):3153-3157. doi: 10.1021/acs.orglett.9b00849. Epub 2019 Apr 18.
A Cu(OAc)-promoted cascade reaction of malonate-tetherd acyl oximes with indoles, indole-2-alcohols, or indole-2-carboxmides provides facile access to polysubstituted 3-pyrrolin-2-ones. The reaction features the generation of two adjacent electrophilic centers at the same time as cyclization to lactam. The subsequent double addition with nucleophiles followed by oxidation realizes the difunctionalization of the imine sp-carbon and the adjacent α-sp-carbon.
醋酸铜促进的丙二酸连接的酰基肟与吲哚、吲哚 - 2 - 醇或吲哚 - 2 - 甲酰胺的串联反应为多取代的3 - 吡咯啉 - 2 - 酮提供了便捷的合成途径。该反应的特点是在环化形成内酰胺的同时生成两个相邻的亲电中心。随后与亲核试剂的两次加成，再经过氧化，实现了亚胺sp - 碳和相邻α - sp - 碳的双官能化。
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