Regiospecific Aza-Michael Addition of 4-Aryl-1H-1,2,3-triazoles to Chalcones: Synthesis of 2,4-Disubstituted 1,2,3-Triazoles in Basic Medium

被引：12

作者：

Bhagat, Ujjawal Kumar ^{[1
]}

Peddinti, Rama Krishna ^{[1
]}

机构：

[1] Indian Inst Technol Roorkee, Dept Chem, Roorkee 247667, Uttarakhand, India

来源：

SYNLETT | 2018年 / 29卷 / 01期

关键词：

triazoles; chalcones; aza-Michael addition; heterocyclic compounds; AZIDE-ALKYNE CYCLOADDITION; RUTHENIUM-CATALYZED CYCLOADDITION; FREE CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; TERMINAL ALKYNES; DIRECT ACCESS; REACTIVITY; EFFICIENT; LIGATION; KETONES;

D O I：

10.1055/s-0036-1588567

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel metal-free and base-mediated method to display the donor ability of 1,2,3-triazoles for the synthesis of 2,4-disubstituted 1,2,3-triazoles has been developed. A DABCO-promoted aza-Michael addition of 4-aryl NH-1,2,3-triazoles to ,-unsaturated ketones (chalcones) is presented. The reactions proceeded with complete regiospecificity in a 3:1 mixture of acetonitrile and methanol at 85 degrees C to provide 2,4-disubstituted 1,2,3-triazoles as Michael adducts, and the addition products 1,3-diaryl-(4-aryl-2H-1,2,3-triazol-2-yl)propan-1-ones were isolated in high yields.

引用

页码：99 / 105

页数：7

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