Novel one-step synthesis of 2-carbonyl/thiocarbonyl isoindolinones and mechanistic disclosure on the rearrangement reaction of o-phthalaldehyde with amide/thioamide analogs

被引：41

作者：

Wan, Jieping ^{[1
]}

Wu, Bin ^{[1
]}

Pan, Yuanjiang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

TETRAHEDRON | 2007年 / 63卷 / 38期

基金：

中国国家自然科学基金;

关键词：

2-carbonyl isoindolinone; 2-thiocarbonyl isoindolinone; rearrangement; mechanism;

D O I：

10.1016/j.tet.2007.07.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rearrangement reaction of o-phthalaldehyde with urea/thiourea analogs or amides/thioamides under the catalysis of TMSC1 (trimethylchlorosilane) is described, whereby a series of 2-carbonyl isoindolinones and 2-thiocarbonyl isoindolinones are afforded. This is the first time that the N-carbonyl/thiocarbonyl isoindolinones are synthesized in a single step from o-phthalaldehyde. Similar reactions using primary amines also proceed smoothly to give corresponding N-alkyl or N-aryl isoindolinones in this mild catalytic system. The mechanism of this kind of rearrangement is discussed based on new evidences observed from the ESI-MS time-interval monitoring of the full reaction course and deuterium exchange experiments. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：9338 / 9344

页数：7

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