Synthesis of fluorescent trisubstituted oxazoles via a facile tandem Staudinger/aza-Wittig/isomerization reaction

被引：15
|
作者：
Xie, Hai [1 ,2 ]
Rao, Yong [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
[2] Shanxi Datong Univ, Coll Chem & Chem Engn, Datong 037009, Shanxi, Peoples R China
来源：
DYES AND PIGMENTS | 2017年 / 139卷
基金：
中国国家自然科学基金;
关键词：
Oxazole; Azide; Aza-Wittig reaction; Fluorescence property; Isomerization; AZA-WITTIG REACTION; 2,4,5-TRISUBSTITUTED OXAZOLES; WITTIG/MICHAEL/ISOMERIZATION REACTION; EFFICIENT SYNTHESIS; AMINO-ACIDS; DERIVATIVES; CYCLIZATION; KETONES; IODINE; DISCOVERY;
D O I：
10.1016/j.dyepig.2016.12.040
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A new facile synthesis of trisubstituted oxazoles starting from azides was developed. The reactions of azides with triphenyl phosphine afforded the corresponding 2,4,5-trisubstituted oxazole derivatives via tandem Staudinger, aza-Wittig and isomerization reaction either thermally or under basic conditions. Properties of the oxazole derivatives were surveyed and some of the examples showed reasonable fluorescence. The greatest fluorescence intensity was observed when the 2- and the 5- substituents on the oxazole ring were aromatic groups (with epsilon = 23-3.0 x 10(4) mol(-1) dm(3) cm(-1) and Phi = 0.25-0.29 relative to quinine sulphate). However, the fluorescence intensity was diminished when either the 2- or the 5-substituent was H or alkyl. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：440 / 447
页数：8
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