Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles

被引：37

作者：

Yoshimura, Akira ^{[1
]}

Nguyen, Khiem C. ^{[1
]}

Klasen, Scott C. ^{[1
]}

Postnikov, Pavel S. ^{[2
]}

Yusubov, Mekhman S. ^{[2
]}

Saito, Akio ^{[3
]}

Nemykin, Victor N. ^{[1
]}

Zhdankin, Viktor V. ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA

[2] Tomsk Polytech Univ, Tomsk 634050, Russia

[3] Tokyo Univ Agr & Technol, Inst Engn, Div Appl Chem, Koganei, Tokyo 1848588, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 09期

基金：

美国国家科学基金会; 俄罗斯科学基金会;

关键词：

1; 2; 4-oxadiazoles; cyclization; heterocycles; iodine; oxidation; OXIDES; CYCLOADDITION; GENERATION; ALKENES; ISOXAZOLINES; DERIVATIVES; REAGENTS; OXIMES;

D O I：

10.1002/ajoc.201600247

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient procedure for oxidative cycloaddition of aldoximes with nitriles using stoichiometric or catalytic amounts of hypervalent iodine(III) reagent IBA-OTf (2-iodosylbenzoic acid triflate) has been developed. This efficient procedure works well for the preparation of various 1,2,4-oxadiazoles in generally high yields under mild reaction conditions. The actual oxidant in this reaction, IBA-OTf, is prepared from 2-iodosylbenzoic acid (IBA) and trifluoromethanesulfonic acid (TfOH) or it can be generated in situ from 2-iodobenzoic acid and m-chloroperoxybenzoic acid (m-CPBA) in the presence of TfOH. The nature of hydroxy(aryl)iodonium species, generated in situ from 2-iodobenzoic acid, m-CPBA, and TfOH under catalytic reaction conditions, has been confirmed by (HNMR)-H-1 spectroscopy, ESI-mass spectrometry, and by X-ray diffraction.

引用

页码：1128 / 1133

页数：6

共 45 条

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