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用于构建二氢异喹啉-1(2H)-酮和异喹啉-1,3(2H,4H)-二酮的取代N-烯丙基苯甲酰胺的级联烷基化反应

Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones.

作者信息

Qian Ping, Du Bingnan, Jiao Wei, Mei Haibo, Han Jianlin, Pan Yi

机构信息

School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China.

School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China; Institute for Chemistry & BioMedical Sciences, Nanjing University, Nanjing, 210093, China.

出版信息

Beilstein J Org Chem. 2016 Feb 17;12:301-8. doi: 10.3762/bjoc.12.32. eCollection 2016.

Abstract

An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C-C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield.

摘要

已经开发了一种以N-烯丙基苯甲酰胺衍生物为起始原料合成4-烷基取代二氢异喹啉-1(2H)-酮的氧化反应。自由基烷基芳基化反应通过烷基化和分子内环化序列进行。发现碳-碳双键上的取代基对反应的进行起着关键作用,能够以良好的化学产率得到预期产物。此外,N-甲基丙烯酰基苯甲酰胺也是当前反应的合适底物,并能以良好的产率提供烷基取代的异喹啉-1,3(2H,4H)-二酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/e9b89cfd3eff/Beilstein_J_Org_Chem-12-301-g002.jpg

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