Regioselective Three-Component Reaction of Pyridine N-Oxides, Acyl Chlorides, and Cyclic Ethers

被引：26

作者：

Jones, D. Heulyn ^{[1
]}

Kay, Steven T. ^{[1
]}

McLellan, Jayde A. ^{[1
]}

Kennedy, Alan R. ^{[1
]}

Tomkinson, Nicholas C. O. ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Thomas Graham Bldg,295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 13期

基金：

英国工程与自然科学研究理事会;

关键词：

HETEROCYCLES; DIVERSITY; DISCOVERY; ANALOGS;

D O I：

10.1021/acs.orglett.7b01481

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel three-component reaction of pyridine N-oxides, acyl chlorides, and cyclic ethers is described. Treatment of an electron-deficient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25-50 degrees C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic-labeling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

引用

页码：3512 / 3515

页数：4

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