Regioselective Synthesis of 1,4,5-Trisubstituted-1,2,3-Triazoles from Aryl Azides and Enaminones

被引：27
|
作者：
De Nino, Antonio [1 ]
Algieri, Vincenzo [1 ]
Talllarida, Matteo A. [1 ]
Constanzo, Paola [1 ]
Pedron, Manuel [2 ]
Tejero, Tomas [3 ]
Merino, Pedro [2 ]
Maiuolo, Loredana [1 ]
机构：
[1] Univ Calabria, Dipartimento Chim & Tecnol Chim, Via P Bucci,Cubo 12C, I-87036 Arcavacata Di Rende, CS, Italy
[2] Univ Zaragoza, Inst Biocomputac & Fis Sistemas Complejos BIFI, E-50009 Zaragoza, Spain
[3] Univ Zaragoza, CSIC, ISQCH, E-50009 Zaragoza, Aragon, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 33期
关键词：
Azides; Enaminones; Dipolar cycloadditions; Ionic liquids; Nitrogen heterocycles; CYCLOADDITION REACTIONS; 1.3-DIPOLARE CYCLOADDITIONEN; 1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY; IONIC LIQUID; 1,2,3-TRIAZOLES; TRANSFORMATIONS; CATALYST; NITRONES;
D O I：
10.1002/ejoc.201900889
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A total regioselective synthesis of 1,4,5-trisubstituted-1,2,3-triazoles from aryl azides and enaminones is reported. The use of an ionic liquid in the presence of water and trimethylamine is crucial for the progress of the reaction. The process, consisting of a cascade starting with a water-promoted 1,3-dipolar cycloaddition (in agreement with DFT calculations) followed by a base-promoted retro-aza-Michael reaction, shows a completely different reactivity to previously reported base-promoted reactions between enaminones and sulfonyl azides only leading to disubstituted triazoles. Such reactivity, reported herein, allows preparation of trisubstituted triazoles in a complete regioselective way.
引用
收藏
页码：5725 / 5731
页数：7
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