One-pot synthesis and the fluorescent behavior of 4-acetyl-5-methyl-1,2,3-triazole regioisomers

被引：96

作者：

Kamalraj, V. R. ^{[1
]}

Senthil, S. ^{[1
]}

Kannan, P. ^{[1
]}

机构：

[1] Anna Univ, Dept Chem, Madras 600025, Tamil Nadu, India

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2008年 / 892卷 / 1-3期

关键词：

1,3-Cycloaddition; 1,2,3-Triazole; Azide; Acetyl acetone; Fluorescence;

D O I：

10.1016/j.molstruc.2008.05.028

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of novel 4-acetyl-5-methyl-1,2,3-triazole exclusively with 1,4 regioisomers were synthesized via 1,3-dipolar cycloaddition with high yield from azide and acetyl acetone in the presence of a base, under warm condition in ethanol in a short duration. All the compounds were characterized by using FT-IR and NMR spectroscopic techniques. The isomer purity has been confirmed by means of HPLC. The reaction is affected by the electronic effects; triazole with electron withdrawing substituent reacts faster with maximum yield of 90% compare to the electron donating substituent. All the compounds show fluorescent behavior. Among them, the 1-[4-(cyano)phenyl]-4-acetyl-5-methyl-1,2,3-triazole remarkably shows dual emission in the chloroform solvent. (C) 2008 Elsevier B.V. All rights reserved.

引用

页码：210 / 215

页数：6

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