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电化学区域选择性硒化/氧化 N-烷基异喹啉鎓盐通过双 C(sp)-H 键官能化。

Electrochemical regioselective selenylation/oxidation of N-alkylisoquinolinium salts via double C(sp)-H bond functionalization.

机构信息

School of Chemistry and Chemical Engineering and Guangdong Cosmetics Engineering & Technology Research Center, Guangdong Pharmaceutical University, Zhongshan 528458, China.

出版信息

Chem Commun (Camb). 2020 Dec 18;56(97):15325-15328. doi: 10.1039/d0cc06778d. Epub 2020 Nov 19.

Abstract

An efficient, novel, and environmentally friendly electrochemical regioselective selenylation/oxidation of N-alkylisoquinolinium salts via double C(sp)-H bond functionalization under undivided electrolytic conditions has been developed. A series of selenide isoquinolones were easily accessed through this sustainable and clean electrochemical system. The present protocol was further extended to afford selenide quinolones and 1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-ones. Furthermore, antiviral bioassays demonstrated that compound 3j exhibited excellent antiviral activity against tobacco mosaic virus (TMV), and its inhibition rate was up to 90%.

摘要

开发了一种在非分隔电解条件下通过双重 C(sp)-H 键官能化实现 N-烷基异喹啉鎓盐的高效、新颖且环保的电化学区域选择性硒化/氧化方法。通过这个可持续和清洁的电化学体系,很容易获得一系列硒代异喹啉酮。本方案进一步扩展到得到硒代喹啉酮和 1,3-二甲基-1H-苯并[d]咪唑-2(3H)-酮。此外,抗病毒生物测定表明,化合物 3j 对烟草花叶病毒(TMV)表现出优异的抗病毒活性,其抑制率高达 90%。

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