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

共 50 条

[41] Metal-free visible-light-catalyzed synthesis of 3-methyl-3,4-dihydroisoquinolin-1(2H)-one: mechanism, DFT calculation and optical properties
Zou, Shuai
Pan, Li
Xue, Tian
Huang, Huang
Geng, Shu
Ding, Jun-Jie
Fu, Fei-Yan
Huang, Feng
CHEMICAL PAPERS, 2021, 75 (08): : 4069 - 4074
[42] Synthesis and Antiarrhythmic and Hemostatic Activity of [3,3-Dialkyl-3, 4-Dihydroisoquinolin-1(2H )-Ylidene]-N-Alkylacetamides
O. V. Gashkova
A. G. Mikhailovskii
I. P. Rudakova
A. V. Starkova
A. S. Yusov
Pharmaceutical Chemistry Journal, 2019, 53 : 507 - 510
[43] Intramolecular Diels-Alder Furan-Mediated Synthesis of 8-Aryl-3,4-dihydroisoquinolin-1(2H)-ones, Convenient Precursors of Indeno[1,2,3-ij] iso-quinolines
Treus, Monica
Harwood, Laurence M.
Estevez, Juan C.
Salas, Cristian
Drew, Michael G. B.
Estevez, Ramon J.
SYNLETT, 2013, 24 (17) : 2221 - 2224
[44] Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate
Yadav, JS
Reddy, BVS
Reddy, KB
Raj, KS
Prasad, AR
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (16): : 1939 - 1941
[45] EFFICIENT SYNTHESIS OF SOME 3-ARYLISOQUINOLIN-1(2H)-ONES
Saeed, Aamer
Ashraf, Zaman
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (08) : 967 - 972
[46] Efficient synthesis of some 3-arylisoquinolin-1(2H)-ones
Aamer Saeed
Zaman Ashraf
Chemistry of Heterocyclic Compounds, 2008, 44
[47] THE CHEMISTRY OF PHTHALIDE-3-CARBOXYLIC ACID .6. THE STEREOCHEMISTRY OF SOME 3-AMINO(ARYL)METHYLPHTHALIDES AND THE DERIVED 3-ARYL-4-HYDROXY-3,4-DIHYDROISOQUINOLIN-1(2H)-ONES
COLLINS, PR
JANOWSKI, WK
PRAGER, RH
AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (04) : 549 - 559
[48] Reaction of (Z)-2-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]-N-(2,4-dimethylphenyl)acetamides with ninhydrin
A. G. Mikhailovskii
A. S. Yusov
D. V. Korchagin
O. V. Gashkova
Russian Journal of Organic Chemistry, 2017, 53 : 790 - 792
[49] Synthesis of 3,4-dihydrobenzo[g]isoquinoline-1(2H)-ones and 3,4-dihydroisoquinoline-1 (2H) ones skeleton via intramolecular electrophilic cyclization
Tsai, MR
Hung, TC
Chen, BF
Cheng, CC
Chang, NC
TETRAHEDRON, 2004, 60 (47) : 10637 - 10644
[50] Reaction of (Z)-2-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]-N-(2,4-dimethylphenyl)acetamides with ninhydrin
Mikhailovskii, A. G.
Yusov, A. S.
Korchagin, D. V.
Gashkova, O. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (05) : 790 - 792

← 1 2 3 4 5 →