IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines

被引：21

作者：

Gao, Peng ^{[1
,2
]}

Chen, Huai-Juan ^{[1
]}

Bai, Zi-Jing ^{[1
]}

Zhao, Mi-Na ^{[1
]}

Yang, Desuo ^{[1
]}

Wang, Juan ^{[1
]}

Wang, Ning ^{[1
]}

Du, Lele ^{[1
]}

Guan, Zheng-Hui ^{[2
]}

机构：

[1] Baoji Univ Arts & Sci, Shaanxi Key Lab Phytochem, Coll Chem & Chem Engn, Baoji 721013, Shaanxi, Peoples R China

[2] Northwest Univ, Dept Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Xian 710127, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 12期

基金：

中国博士后科学基金; 美国国家科学基金会;

关键词：

C-H FUNCTIONALIZATIONS; HYPERVALENT IODINE; NATURAL-PRODUCTS; ACID IBX; REARRANGEMENT; MECHANISM; REAGENTS; KETONES; FURANS; SCOPE;

D O I：

10.1021/acs.joc.0c00625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and alpha-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.

引用

页码：7939 / 7951

页数：13

共 4 条

[1] Synthesis of 2,3-Disubstituted pyrroles by Lewis acid promoted cyclization of N-Sulfonyl vinylogous carbamates and amides
Rustin, Gavin J.
Donahue, Matthew G.
TETRAHEDRON LETTERS, 2023, 122
[2] Facile Synthesis of 2,3-Disubstituted Indoles by NBS/CuCl Mediated Oxidative Cyclization of N-Aryl Enamines
Hu, Fang-Zhi
Zhao, Si-Han
Chen, Hui
Yu, Shuo-Wen
Xu, Xiao-Ying
Yuan, Wei-Cheng
Zhang, Xiao-Mei
CHEMISTRYSELECT, 2017, 2 (04): : 1409 - 1412
[3] Metal-free dual sp3 C-H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
Gao, Qing-He
Fei, Zhuan
Zhu, Yan-Ping
Lian, Mi
Jia, Feng-Cheng
Liu, Mei-Cai
She, Neng-Fang
Wu, An-Xin
TETRAHEDRON, 2013, 69 (01) : 22 - 28
[4] Metal-free iodic acid-triggered cascade cyclization of alkenes with N-hydroxyphthalimide: A simple and mild access to aminooxylated 3,3-disubstituted 2-oxindoles
Zhang, Ming-Zhong
Li, Yan
Zhang, Jiao
Bao, Xin
Yuan, Ya-Wen
Chen, Jie
Chen, Feng-Gui
TETRAHEDRON LETTERS, 2021, 67

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