Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3+2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers

被引：26

作者：

Park, Sangjune ^{[1
]}

Kim, Hyunseok ^{[1
]}

Son, Jeong-Yu ^{[1
]}

Um, Kyusik ^{[1
]}

Lee, Sooho ^{[1
]}

Baek, Yonghyeon ^{[1
]}

Seo, Boram ^{[1
]}

Lee, Phil Ho ^{[1
]}

机构：

[1] Kangwon Natl Univ, Dept Chem, Chunchon 24341, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 19期

基金：

新加坡国家研究基金会;

关键词：

C-H AMINATION; FACILE SYNTHESIS; TRANSANNULATION; 1,2,3-THIADIAZOLES; FUNCTIONALIZATION; INSERTION; 1,2,3-TRIAZOLES; DIAMINATION; CARBENOIDS; TRIAZOLES;

D O I：

10.1021/acs.joc.7b01714

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Cu-catalyzed, formal aza-[3 + 2] cycloaddition reaction of pyridine derivatives with alpha-diazo oxime ethers in trifluoroethanol was used to synthesize imidazopyridines via the release of molecular nitrogen and elimination of alcohol. These methods enabled modular synthesis of a wide range of N-heterobicyclic compounds such as imidazopyridazines, imidazopyrimidines, and imidazopyrazines with an alpha-imino Cu-carbenoid generated from the alpha-diazo oxime ethers and copper.

引用

收藏

页码：10209 / 10218

页数：10

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