Direct C-4 alkylation of quinazoline N-oxides with ethers via an oxidative cross-coupling reaction under metal-free conditions

被引：19

作者：

Yang, Qin

Lou, Minhao

Yin, Zhijian

Deng, Zhihong

Ding, Qiuping ^{[1
]}

Peng, Yiyuan ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Jiangxi, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 45期

基金：

中国国家自然科学基金;

关键词：

C-H ARYLATION; ONE-STEP CONVERSION; EFFICIENT ROUTE; QUINOLINE; BONDS; ARYL; ALKENES; MILD; FUNCTIONALIZATION; ARYLHYDRAZINES;

D O I：

10.1039/c8ob01429a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient protocol for the direct C-4 alkylation of quinazoline-3-oxides via radical oxidative coupling between quinazoline 3-oxides and ethers in the presence of TBHP was developed. The reaction proceeded smoothly under metal-free conditions, which provided quinazoline-containing heterocyclic molecules in moderate to good yields.

引用

页码：8724 / 8731

页数：9

共 50 条

[21] Synthesis of Alkyl-Substituted Pyrazine N-Oxides by Transition-Metal-Free Oxidative Cross-Coupling Reactions
Lai, Miao
Li, Yuan
Wu, Zhiyong
Zhao, Mingqin
Ji, Xiaoming
Liu, Pengfei
Zhang, Xiaoping
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (06) : 1118 - 1123
[22] Tandem Denitrogenation Oxidative Coupling Reaction of Phenyl Vinyl Azides and Cyclic Ethers Under Metal-Free Conditions
Mou, Dan
Li, Qian
Du, Zhengyin
CHEMISTRYSELECT, 2023, 8 (01):
[23] Direct C-C Bond Formation through Decarboxylative Oxidative Cross-Coupling of Cinnamic Acids with Amides under Metal-Free Condition
Lu, Xiaobiao
Xiao, Xi
Wan, Changfeng
Wang, Zhiyong
Liu, Jinbiao
ACTA CHIMICA SINICA, 2021, 79 (06) : 751 - 754
[24] Metal-free cross-coupling reaction of aldehydes with disulfides by using DTBP as an oxidant under solvent-free conditions
Zeng, Jing-Wen
Liu, Yi-Chen
Hsieh, Ping-An
Huang, Yu-Ting
Yi, Chih-Lun
Badsara, Satpal Singh
Lee, Chin-Fa
GREEN CHEMISTRY, 2014, 16 (05) : 2644 - 2652
[25] Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions
Song, Yang
Zhang, Hao
Guo, Jiabao
Shao, Yifei
Ding, Yuzhou
Zhu, Li
Yao, Xiaoquan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (44) : 5914 - 5921
[26] Highly chemoselective deoxygenation of N-heterocyclic N-oxides under transition metal-free conditions
Kim, Se Hyun
An, Ju Hyeon
Lee, Jun Hee
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (16) : 3735 - 3742
[27] Direct cross-dehydrogenative coupling reactions of imidazopyridines and 1-naphthylamines with ethers under metal-free conditions
Dong, Zhe
Liu, Yu
Zhou, Chen-Wei
Huang, Jun-Jian
Guo, Tao
Wang, Yun
SYNTHETIC COMMUNICATIONS, 2020, 50 (13) : 1972 - 1981
[28] Metal-free C-N cross-coupling of electrophilic compounds and N-haloimides
Zhang, Luyan
Li, Yanru
Jin, Long-Yi
Liang, Fushun
RSC ADVANCES, 2015, 5 (80) : 65600 - 65603
[29] Studies on pyrazines .31. Alkylation of chloropyrazine N-oxides by nickel-catalyzed cross-coupling reaction with dialkylzincs
Sato, N
Matsuura, T
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (04) : 1047 - 1049
[30] Benzylation of heterocyclic N-oxides via direct oxidative cross-dehydrogenative coupling with toluene derivatives
Wan, L.
Qiao, K.
Sun, X. N.
Di, Z. C.
Fang, Z.
Li, Z. J.
Guo, K.
NEW JOURNAL OF CHEMISTRY, 2016, 40 (12) : 10227 - 10232

← 1 2 3 4 5 →