The effect of microwave irradiation on carbodiimide-mediated esterifications on solid support

被引：66

作者：

Stadler, A ^{[1
]}

Kappe, CO ^{[1
]}

机构：

[1] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria

来源：

TETRAHEDRON | 2001年 / 57卷 / 18期

基金：

奥地利科学基金会;

关键词：

combinatorial chemistry; solid-phase synthesis; microwave-enhanced chemistry; O-acylisourea; anhydrides;

D O I：

10.1016/S0040-4020(01)00260-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The esterification of a polymer-supported alcohol (PS Wang resin) with benzoic acid was investigated using microwave irradiation. Activation of the carboxylic acid was carried out using diisopropylcarbodiimide, either via the O-acylisourea or symmetrical anhydride protocols. In the microwave-assisted solid-phase coupling using the O-acylisourea method the main product of the reaction was 1-benzoyl-1,3-diisopropylurea, formed by rearrangement of the thermolabile isourea intermediate. On the other hand, significant rate enhancements were observed for the coupling of benzoic anhydride to Wang resin using microwave hash heating in 1-methyl-2-pyrrolidone as solvent. Reaction times were reduced from 2 to 3 days using conventional conditions, to 10 min by microwave dielectric heating. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3915 / 3920

页数：6

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