A novel four-component reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives

被引：85

作者：

Ramazani, Ali ^{[1
]}

Shajari, Nahid ^{[1
]}

Mahyari, Amir ^{[1
]}

Ahmadi, Yavar ^{[1
]}

机构：

[1] Zanjan Univ, Dept Chem, Zanjan, Iran

来源：

MOLECULAR DIVERSITY | 2011年 / 15卷 / 02期

基金：

美国国家科学基金会;

关键词：

(N-isocyanimino)triphenylphosphorane; Aromatic carboxylic acid; Cyclobutanone; Benzyl amine; 1,3,4-oxadiazole; aza-Wittig reaction; 4CC; MCR; STABILIZED PHOSPHORUS YLIDES; POLYMER-SUPPORTED REAGENTS; ONE-POT; STEREOSELECTIVE-SYNTHESIS; ALKYL ISOCYANIDES; (N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE; ACID;

D O I：

10.1007/s11030-010-9275-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The 1:1 imine intermediate generated by the addition of benzyl amine to cyclobutanone is trapped by (N-isocyanimino)triphenylphosphorane in the presence of an aromatic carboxylic acid leads to the formation of the corresponding iminophosphorane intermediate. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives, were produced in excellent yields.

引用

页码：521 / 527

页数：7

共 23 条

[21] A simple and efficient one step synthesis of 1,3,4-oxadiazoles utilizing polymer-supported reagents and microwave heating
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[22] Reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of bidentate nucleophiles
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Hossaini, Zinatossadat
Sabbaghan, Maryam
[J]. MOLECULAR DIVERSITY, 2006, 10 (03) : 479 - 482

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