Copper-catalyzed aerobic oxidative decarboxylative amination of arylacetic acids: a facile access to 2-arylquinazolines

被引：33

作者：

Yan, Yizhe ^{[1
,2
]}

Shi, Miaomiao ^{[1
]}

Niu, Bin ^{[1
]}

Meng, Xiangping ^{[1
]}

Zhu, Changrui ^{[1
]}

Liu, Gengyao ^{[1
]}

Chen, Ting ^{[1
]}

Liu, Yanqi ^{[1
]}

机构：

[1] Zhengzhou Univ Light Ind, Sch Food & Biol Engn, Zhengzhou 450000, Peoples R China

[2] Collaborat Innovat Ctr Food Prod & Safety, Zhengzhou, Henan Province, Peoples R China

来源：

RSC ADVANCES | 2016年 / 6卷 / 42期

基金：

中国国家自然科学基金;

关键词：

ALIPHATIC CARBOXYLIC-ACIDS; ALPHA-AMINO-ACIDS; RECEPTOR TYROSINE KINASE; QUINAZOLINE DERIVATIVES; HYDROXYPHENYLACETIC ACIDS; PHENYLACETIC ACIDS; ACRIDONE ALKALOIDS; COUPLING REACTIONS; CASCADE SYNTHESIS; AQUEOUS-SOLUTION;

D O I：

10.1039/c6ra04195g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient copper-catalyzed oxidative decarboxylative amination of arylacetic acids with 2-aminobenzoketones and ammonium acetate under an oxygen atmosphere was first developed. This reaction represents a novel avenue for 2-arylquinazolines in good to excellent yields via multiple C-N bond formations. This protocol features inexpensive copper as the catalyst, molecular oxygen as the sole oxidant, H2O and CO2 as wastes, and a broad substrate scope.

引用

页码：36192 / 36197

页数：6

共 50 条

[1] Facile access to evodiakine enabled by aerobic copper-catalyzed oxidative rearrangement
Su, Yiting
Huang, Gaofeng
Ye, Fu
Qiao, Panpan
Ye, Jinxiang
Gao, Yu
Chen, Haijun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (39) : 8811 - 8815
[2] Efficient synthesis of 2-arylquinazolines via copper-catalyzed dual oxidative benzylic C–H aminations of methylarenes
Li-Yan Liu
Yi-Zhe Yan
Ya-Jie Bao
Zhi-Yong Wang
Chinese Chemical Letters, 2015, 26 (10) : 1216 - 1220
[3] Copper-catalyzed oxidative amination of methanol to access quinazolines
Satish, Gandhesiri
Polu, Ashok
Kota, Laxman
Ilangovan, Andivelu
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (19) : 4774 - 4782
[4] Intermediacy of Copper(I) under Oxidative Conditions in the Aerobic Copper-Catalyzed Decarboxylative Thiolation of Benzoic Acids
Green, Kerry-Ann
Hoover, Jessica M.
ACS CATALYSIS, 2020, 10 (03) : 1769 - 1782
[5] Aerobic copper-catalyzed decarboxylative thiolation
Li, Minghao
Hoover, Jessica M.
CHEMICAL COMMUNICATIONS, 2016, 52 (56) : 8733 - 8736
[6] Copper-Catalyzed Aerobic Oxidative/Decarboxylative Phosphorylation of Aryl Acrylic Acids with P(III)-Nucleophiles
Xiong, Biquan
Si, Lulu
Zhu, Longzhi
Liu, Yu
Xu, Weifeng
Tang, Ke-Wen
Yin, Shuang-Feng
Qian, Peng-Cheng
Wong, Wai-Yeung
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12502 - 12518
[7] Copper-catalyzed oxidative decarboxylative coupling of α-keto acids and sulfoximines
Pimpasri, Chaleena
Sumunnee, Ladawan
Yotphan, Sirilata
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (20) : 4320 - 4327
[8] Efficient synthesis of 2-arylquinazolines via copper-catalyzed dual oxidative benzylic C-H aminations of methylarenes
Liu, Li-Yan
Yan, Yi-Zhe
Bao, Ya-Jie
Wang, Zhi-Yong
CHINESE CHEMICAL LETTERS, 2015, 26 (10) : 1216 - 1220
[9] Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by Copper-Catalyzed Oxidative Coupling
Gao, Bao
Xie, Yinjun
Shen, Zhiqiang
Yang, Lei
Huang, Hanmin
ORGANIC LETTERS, 2015, 17 (20) : 4968 - 4971
[10] Copper-Catalyzed Oxidative Decarboxylative Couplings of Sulfoximines and Aryl Propiolic Acids
Priebbenow, Daniel L.
Becker, Peter
Bolm, Carsten
ORGANIC LETTERS, 2013, 15 (24) : 6155 - 6157

← 1 2 3 4 5 →