Direct Synthesis of Disubstituted 3-Isoquinolinone Derivatives through the Construction of C-N, C=O, and C(sp2)-C(sp3) Bonds under Transition-Metal-Free Conditions

被引：11

作者：

Shi, Jianyi ^{[1
]}

Chen, Xia ^{[1
]}

Huang, Jingyun ^{[1
]}

Lu, Yantong ^{[1
]}

Yang, Zhendong ^{[1
]}

Zhong, Mingli ^{[2
]}

Zhu, Zhongzhi ^{[1
]}

Chen, Xiuwen ^{[1
]}

机构：

[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Peoples R China

[2] Guilin Med Univ, Pharmacol Lab Prevent & Treatment High Incidence D, Guilin 541199, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 03期

基金：

中国国家自然科学基金;

关键词：

acetophenone; dearomatization; nitromethane; trifunctionalization; CATALYZED HYDROXYLATION; EFFICIENT SYNTHESIS; ARYL HALIDES; FUNCTIONALIZATION; ISOQUINOLINES; OXIDATION; PHENOLS;

D O I：

10.1002/ejoc.202201231

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient three-component cascade coupling reaction of 3-haloisoquinolines, haloalkanes, and sp(3)-carbon nucleophiles (acetophenone or nitromethane) led to a series of structurally novel 1,2-disubstituted-3-isoquinolinones through the formation of C(sp(3))-C(sp(2)), C-N, and C=O bonds. The NaOAc-promoted reaction described in this work is simple to operate, environment friendly, and highly selective.

引用

页数：5

共 50 条

[1] Oxidative radical cascade cyclization involving C(sp3)-C(sp3), C(sp3)-C(sp2) and C(sp2)-N bonds formation: direct construction of cyano and methyl substituted polyheterocycles
Shang, Jia-Qi
Wang, Shi-Sheng
Fu, Hong
Li, Yi
Yang, Tao
Li, Ya-Min
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (12): : 1945 - 1949
[2] Boron carbonitride photocatalysts for direct decarboxylation: the construction of C(sp3)-N or C(sp3)-C(sp2) bonds with visible light
Shi, Jiale
Yuan, Tao
Wang, Rong
Zheng, Meifang
Wang, Xinchen
GREEN CHEMISTRY, 2021, 23 (11) : 3945 - 3949
[3] Aminodealkenylation: Ozonolysis and copper catalysis convert C(sp3)-C(sp2) bonds to C(sp3)-N bonds
He, Zhiqi
Moreno, Jose Antonio
Swain, Manisha
Wu, Jason
Kwon, Ohyun
SCIENCE, 2023, 381 (6660) : 877 - 885
[4] Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners
Li, Minyan
Berritt, Simon
Matuszewski, Lucas
Deng, Guogang
Pascual-Escudero, Ana
Panetti, Grace B.
Poznik, Michal
Yang, Xiaodong
Chruma, Jason J.
Walsh, Patrick J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) : 16327 - 16333
[5] Dealkenylative Thiylation of C(sp3)-C(sp2) Bonds
Smaligo, Andrew J.
Kwon, Ohyun
ORGANIC LETTERS, 2019, 21 (21) : 8592 - 8597
[6] Oxidative cross-coupling of pyridine N-oxides and ethers between C(sp2)-H/C(sp3)-H bonds under transition-metal-free conditions
Sun, Wei
Xie, Zuguang
Liu, Jie
Wang, Lei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (15) : 4596 - 4604
[7] Metal-free synthesis of indolizines through oxidative C-C and C-N bond formations of C (sp3)-H bonds
Reddy, N. Naresh Kumar
Mohan, Darapaneni Chandra
Adimurthy, Subbarayappa
TETRAHEDRON LETTERS, 2016, 57 (10) : 1074 - 1078
[8] Palladium Catalysis: Dependence of the Efficiency of C-C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part A: the C(sp2)-C(sp2), C(sp2)-C(sp3) and C(sp3)-C(sp3) Bonds
Le Bras, Jean
Muzart, Jacques
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3727 - 3773
[9] The Construction of C-N, C-O, and C(sp2)-C(sp3) Bonds from Fluorine-Substituted 2-Aryl Benzazoles for Direct Synthesis of N-, O-, C-Functionalized 2-Aryl Benzazole Derivatives
Zhou, Quan
Hong, Xi
Cui, He-Zhen
Huang, Shuang
Yi, Ying
Hou, Xiu-Feng
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6363 - 6372
[10] Arylation of Terminal Alkynes: Transition-Metal-Free Sonogashira- Type Coupling for the Construction of C(sp)-C(sp2) Bonds
Ye, Mingxing
Hou, Mengyuan
Wang, Yahao
Ma, Xingxing
Yang, Kai
Song, Qiuling
ORGANIC LETTERS, 2023, 25 (10) : 1787 - 1792

← 1 2 3 4 5 →