One-Pot Synthesis of Isoxazolines from Aldehydes Catalyzed by Iodobenzene

被引：27

作者：

Han, Liuquan ^{[1
]}

Zhang, Bijun ^{[1
]}

Xiang, Changbin ^{[1
]}

Yan, Jie ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310032, Zhejiang, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 04期

关键词：

one-pot synthesis; isoxazolines; iodobenzene; hypervalent iodine intermediate; catalytic cycloaddition; NITRILE OXIDES; CYCLOADDITION; GENERATION; ALDOXIMES; ALKENES; OXIMES; BENZISOXAZOLES; DERIVATIVES; OXIDATIONS; INHIBITORS;

D O I：

10.1055/s-0033-1340464

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes has been developed involving catalytic cycloaddition between nitrile oxides and alkenes, in which iodobenzene is used as the catalyst for the in situ generation of a hypervalent iodine intermediate. In this approach, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by the in situ generated hypervalent iodine intermediate; finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes occurs to provide the isoxazolines in moderate to good yields.

引用

页码：503 / 509

页数：7

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