An Enolate-Mediated Organocatalytic Azide-Ketone [3+2]-Cycloaddition Reaction: Regioselective High-Yielding Synthesis of Fully Decorated 1,2,3-Triazoles

被引：94
作者：
Shashank, Adluri B. [1 ]
Karthik, S. [1 ]
Madhavachary, R. [1 ]
Ramachary, Dhevalapally B. [1 ]
机构：
[1] Univ Hyderabad, Sch Chem, Catalysis Lab, Hyderabad 500046, Andhra Pradesh, India
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 51期
关键词：
azides; click reaction; ketones; organocatalysis; triazoles; RUTHENIUM-CATALYZED CYCLOADDITION; METAL-FREE SYNTHESIS; REGIOSPECIFIC SYNTHESIS; ALKYNE CYCLOADDITION; ONE-POT; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; 1,3-DIPOLAR CYCLOADDITION; BIOLOGICAL PROFILE; DIRECT ARYLATION; CLICK CHEMISTRY;
D O I：
10.1002/chem.201405501
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An enolate-mediated organocatalytic azideketone [3+2]-cycloaddition (OrgAKC) reaction of a variety of enolizable arylacetones and deoxybenzoins with aryl azides was developed for the synthesis of fully decorated 1,4-diaryl-5-methyl(alkyl)-1,2,3-triazoles in excellent yields with high regioselectivity at 25 degrees C for 0.5-6 h. This reaction has an excellent outcome with reference to reaction rate, yield, regioselectivity, operation simplicity, and availability of substrates and catalyst. This reaction has advantages over the previously known metal-mediated reactions.
引用
收藏
页码：16877 / 16881
页数：5
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