One-Pot Synthesis of 4-Quinolone via Iron-Catalyzed Oxidative Coupling of Alcohol and Methyl Arene

被引：13

作者：

Lee, Seok Beom ^{[1
]}

Jang, Yoonkyung ^{[1
]}

Ahn, Jiwon ^{[1
]}

Chun, Simin ^{[1
]}

Oh, Dong-Chan ^{[2
]}

Hong, Suckchang ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Pharm, Res Inst Pharmaceut Sci, Seoul 08826, South Korea

[2] Seoul Natl Univ, Coll Pharm, Nat Prod Res Inst, Seoul 08826, South Korea

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 21期

基金：

新加坡国家研究基金会;

关键词：

ANTITUMOR AGENTS; 2-ARYL-4-QUINOLONES; CYCLIZATION; INHIBITORS; AMIDATION; SCAFFOLD; ARYL;

D O I：

10.1021/acs.orglett.0c03011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we describe the iron(III)-catalyzed oxidative coupling of alcohol/methyl arene with 2-amino phenyl ketone to synthesize 4-quinolone. Alcohols and methyl arenes are oxidized to the aldehyde in the presence of an iron catalyst and di-tert-butyl peroxide, followed by a tandem process, condensation with amine/Mannich-type cyclization/oxidation, to complete the 4-quinolone ring. This method tolerates various kinds of functional groups and provides a direct approach to the synthesis of 4-quinolones from less functionalized substrates.

引用

页码：8382 / 8386

页数：5

共 50 条

[21] A one-pot protocol for iron-catalyzed decarbonylative borylation of aryl and alkyl carboxylic acids
Bai, Mei
Geng, Shasha
Chen, Shuo
Liu, Zhengli
Feng, Zhang
[J]. STAR PROTOCOLS, 2022, 3 (04):
[22] Iron-catalyzed one-pot oxidation/Knoevenagel condensation reaction using air as an oxidant
Huang, Lu-Shan
Lai, Yi-Huan
Yang, Cheng
Xu, Da-Zhen
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (06)
[23] Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols
Putta, Ramachandra Reddy
Chun, Simin
Lee, Seok Beom
Hong, Junhwa
Oh, Dong-Chan
Hong, Suckchang
[J]. RSC ADVANCES, 2021, 11 (30) : 18225 - 18230
[24] Two-Step, One-Pot Pyrrole Synthesis by Iron-Catalyzed Carboamination/Copper-Mediated Cyclization
Murphy, Grace K.
Richards, Corey A.
Applegate, Seth A.
Neely, Jamie M.
[J]. SYNLETT, 2023, 34 (05) : 433 - 436
[25] Highly efficient iron-catalyzed allylation of aromatic aldehydes with allyltriethoxysilane: one-pot and practical synthesis of homoallyl ethers
Yang, Ming-Song
Xu, Li-Wen
Zhang, Fei-Bao
Qiu, Hua-Yu
Jiang, Jian-Xiong
Lai, Guo-Qiao
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2008, 22 (03) : 177 - 180
[26] Iron-catalyzed one-pot synthesis of quinoxalines: Transfer hydrogenative condensation of 2-nitroanilines with vicinal diols
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul
08826, Korea, Republic of
不详
08826, Korea, Republic of
[J]. RSC Adv., 1600, 30 (18225-18230):
[27] One Pot Synthesis of γ-Benzopyranones via Iron-Catalyzed Aerobic Oxidation and Subsequent 4-Dimethylaminopyridine Catalyzed 6-endo Cyclization
Zhai, Di
Chen, Lingzhu
Jia, Minqiang
Ma, Shengming
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) : 153 - 160
[28] One-pot synthesis of polyimides via Ni-catalyzed coupling of bis(chlorophthalimide)s
Shang, Zhenping
Gao, Changlu
Wang, Zhen
Ding, Mengxian
Gao, Lianxun
[J]. EUROPEAN POLYMER JOURNAL, 2007, 43 (05) : 2135 - 2140
[29] One-Pot Synthesis of Benzene and Pyridine Derivatives via Copper-Catalyzed Coupling Reactions
Han, Jianwei
Guo, Xin
Liu, Yafeng
Fu, Yajie
Yan, Rulong
Chen, Baohua
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (15) : 2676 - 2681
[30] Total Synthesis of (-)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization
Bai, Leiyang
Ma, Yinhao
Jiang, Xuefeng
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (49) : 20609 - 20615

← 1 2 3 4 5 →