Preparation of 1-aryl-substituted isoindoline derivatives by sequential Morita-Baylis-Hillman and intramolecular Diels-Alder reactions

被引：14

作者：

Clary, Kristen Nicole ^{[1
]}

Parvez, Masood ^{[1
]}

Back, Thomas George ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; INHIBITORS; POTENT; CYCLIZATIONS; ARYLATION; SERIES;

D O I：

10.1039/b817954a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldimines underwent Morita-Baylis-Hillman reactions with dienes activated by sulfonyl or nitrile groups. The N-allyl or propargyl derivatives of the products were subjected to intramolecular Diels-Alder cycloadditions to produce the corresponding partly saturated 1-arylisoindoline derivatives. The cycloadducts in the nitrile-activated N-propargyl series were aromatized by base-mediated elimination of HCN to afford 1-arylisoindolines, which were in turn oxidized to the corresponding 3-arylisoindolin-1-ones.

引用

页码：1226 / 1230

页数：5

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