Efficient and scalable synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by benzylic oxidation of tetrahydroisoquinoline derivatives using cerium ammonium nitrate (CAN)

被引：0

作者：

Luo, Jiajun ^{[1
]}

Li, Zhilong ^{[1
]}

He, Jiaxin ^{[1
]}

Li, Tong ^{[1
]}

Wu, Daochen ^{[1
]}

Lai, Yang ^{[1
]}

Sun, Haiying ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Med Chem, Jiangsu Key Lab Drug Design & Optimizat, Nanjing 211198, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 20期

关键词：

DIHYDROISOQUINOLONES; ETHERS;

D O I：

10.1039/d4ob00491d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and scalable method for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones through benzylic oxidation of tetrahydroisoquinoline derivatives using a catalytic amount of cerium ammonium nitrate (CAN) and a stoichiometric amount of NaBrO3 as oxidants was developed. The reaction is significantly influenced by the substituent groups on the phenyl ring. While electron-withdrawing groups on the phenyl ring can lower the reactivities of the substrates, electron-donating groups on the phenyl ring can dramatically promote the oxidation rate.

引用

页码：4153 / 4156

页数：4

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