Reaction of Nitrile Oxides with Masked o-Benzoquinones; Synthesis of Highly Functionalized Isoxazolines

被引：19

作者：

Chittimalla, Santhosh Kumar ^{[1
]}

Kuppusamy, Rajesh ^{[1
]}

Thiyagarajan, Kamalraj ^{[1
]}

Bandi, Chennakesavulu ^{[1
]}

机构：

[1] AMRI Singapore Res Ctr, Dept Med Chem, Singapore 117525, Singapore

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 13期

关键词：

Nitrile oxides; Quinones; Cycloaddition; Rearrangement; Heterocycles; 1,3-DIPOLAR CYCLOADDITION REACTIONS; DIELS-ALDER REACTIONS; CONFORMATIONAL FLEXIBILITY; STEREOCHEMICAL ASSIGNMENT; QUINONE CYCLOADDUCTS; BENZONITRILE OXIDE; LINEAR TRIQUINANES; N-OXIDES; CONSTRUCTION; STRATEGY;

D O I：

10.1002/ejoc.201201670

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Masked o-benzoquinones, on reaction with nitrile oxides generated in situ from the corresponding hydroxamoyl chlorides, provide [3+2] cycloaddition products or novel isoxazoline derivatives through an unprecedented rearrangement. The isolated [3+2] cycloadducts could be transformed into the corresponding isoxazoline derivatives in the presence of Et3N and highly functionalized benzisoxazoles in the presence of 4 N HCl.

引用

页码：2715 / 2723

页数：9

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