Synthesis of 3-Acyl-isoxazoles and Δ2-Isoxazolines from Methyl Ketones, Alkynes or Alkenes, and tert-Butyl Nitrite via a Csp3-H Radical Functionalization/Cycloaddition Cascade

被引：44

作者：

Dai, Peng ^{[1
]}

Tan, Xin ^{[1
]}

Luo, Qian ^{[1
]}

Yu, Xiang ^{[1
]}

Zhang, Shuguang ^{[1
]}

Liu, Fang ^{[1
]}

Zhang, Wei-Hua ^{[1
]}

机构：

[1] Nanjing Agr Univ, Coll Sci, Jiangsu Key Lab Pesticide Sci, Nanjing 210095, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 13期

基金：

国家重点研发计划;

关键词：

BOND OXIDATIVE FUNCTIONALIZATION; CATALYZED SYNTHESIS; FACILE SYNTHESIS; ISOXAZOLES; DERIVATIVES; CYCLOADDITION; CYCLIZATION; ALDEHYDES; EFFICIENT;

D O I：

10.1021/acs.orglett.9b01683

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel metal-free tandem Csp(3)-H bond functionalization of ketones and 1,3-dipolar cycloaddition has been developed. An efficient approach to a variety of oxazole and isoxazoline derivatives is demonstrated using the 1,3-dipolar cycloaddition of alkynes and alkenes to nitrile oxides generated by reactions of methyl ketones with tent-butyl nitrite. This new protocol provides access to a variety of isoxazolines with diverse functionalities. An isoxazole generated in this way was found to have significant antifungal activity.

引用

页码：5096 / 5100

页数：5

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