Convenient and efficient access to tri- and tetra-substituted 4-fluoropyridines via a [3+2]/[2+1] cyclization reaction

被引：8

作者：

Tang, Xuejiao ^{[1
]}

Liu, Kun ^{[1
]}

Qu, Zeming ^{[1
]}

Zhan, Junyan ^{[1
]}

Zhu, Rukui ^{[1
]}

Teng, Fan ^{[3
]}

Meng, Lili ^{[1
]}

Huang, Yanmin ^{[1
]}

Huang, Chusheng ^{[1
]}

He, Yimiao ^{[1
]}

Zhu, Qiang ^{[1
,2
]}

机构：

[1] Nanning Normal Univ, Coll Chem & Mat, Guangxi Key Lab Nat Polymer Chem & Phys, Nanning 530001, Peoples R China

[2] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Guangzhou 510530, Peoples R China

[3] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2022年 / 33卷 / 06期

基金：

中国国家自然科学基金;

关键词：

4-Fluoropyridine; gem-Difluorocyclopropene; 3+2]/[2+1] cyclization reaction; DMSO as an oxidant; Regioselectivity; PKM2; modulator; NUCLEOPHILIC AROMATIC FLUORINATION; DIFLUOROCARBENE CHEMISTRY; CYCLOADDITION; DIFLUOROCYCLOPROPENES; DEOXYFLUORINATION; CYCLOPROPENES; FLUORIDES; PYRROLES; SALTS;

D O I：

10.1016/j.cclet.2022.02.031

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A [3 + 2]/[2 + 1] cycloaddition reaction of gem-difluorocyclopropenes is presented, offering a mild and efficient approach to accessing tri- and tetra-substituted 4-fluoropyridines in moderate to good yields with excellent regioselectivity. Multiple synthetic applications, including process-scale reactions, modification of bioactive molecules, derivatization reactions and synthesis of the analogue of the PKM2 modulator, are subsequently described. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

引用

页码：2982 / 2986

页数：5

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