Direct access to 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of allyl ketones with azides

Li, Wenjun; Du, Zhiyun; Huang, Jiayao; Jia, Qianfa; Zhang, Kun; Wang, Jian

doi:10.1039/c4gc00406j

Cited by 105 publications

(26 citation statements)

References 53 publications

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“…More recently, organocatalytic triazole formation has been used as a powerful, albeit less developed, alternative to metal‐catalyzed AAC reactions. The groups of Ramachary16a,h and Bressy,16c as well as our group,16b,d,f,g,j independently reported the organocatalytic regioselective synthesis of substituted 1,2,3‐triazoles through enamine intermediates formed in situ. This method attracted much attention because of the common green features of organocatalysis 17.…”

Section: Methodsmentioning

confidence: 91%

Lewis Base Catalyzed Aerobic Oxidative Intermolecular Azide–Zwitterion Cycloaddition

Wang

2014

Angewandte Chemie

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The discovery of a novel aerobic oxidative intermolecular azide-zwitterion reaction catalyzed by an organocatalyst is presented. It is demonstrated that the merger of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene and electrondeficient olefins generates reactive zwitterion intermediates, which readily participate in cycloaddition reactions with an array of azides, thus providing facile entry to fully or highly substituted 1,2,3-triazole frameworks. The reaction features an excellent substrate scope, and the products are obtained with high yields and excellent regioselectivities. It is demonstrated that some of these products can be transformed into pharmaceutically important agents. In addition to the experimental results, a detailed mechanistic survey is also provided, including MS studies rationalizing the origin of regioselective control.

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Section: Methodsmentioning

confidence: 91%

Lewis Base Catalyzed Aerobic Oxidative Intermolecular Azide–Zwitterion Cycloaddition

Wang

2014

Angewandte Chemie

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“…Wang and coworkers devised an organocatalytic method for the preparation of fully substituted 1,2,3-triazoles by diethylamine-catalyzed reaction of azides and allyl ketones [27].…”

Section: Metal Free Synthesis Of 123-triazolesmentioning

confidence: 99%

1,2,3-Triazoles: Synthesis and Biological Application

Ali¹

2021

Azoles - Synthesis, Properties, Applications and Perspectives

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Among nitrogen-containing heterocyclic compounds, 1,2,3-triazoles are privileged structure motif and received a great deal of attention in academics and industry. Even though absent in nature, 1,2,3-triazoles have found broad applications in drug discovery, organic synthesis, polymer chemistry, supramolecular chemistry, bioconjugation, chemical biology, fluorescent imaging, and materials science. Therefore, the development of facile and straightforward methodology for the synthesis of 1,2,3-triazoles is of noteworthy interest. In this study, emphasis will be given to numerous synthetic approaches for the synthesis of 1,2,3-triazoles, especially the popular click chemistry approach. Furthermore, several biological activities of this promising heterocycle will also be discussed.

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“…In recent years, advancement in enamine mediated organocatalysis has had a significant impact in the field of 1,2,3‐triazole synthesis 8a], [8b] This reaction generally involves the catalytic formation of an enamine intermediate through the reaction of a carbonyl compound 31 and an amine catalyst, followed by its cycloaddition reaction with an organic azide.…”

Section: Organocatalytic Processes Involving Reactions Of Enaminesmentioning

confidence: 99%

“…An organocatalytic approach was first used by Ramachary et al for the synthesis of fused NH ‐1,2,3‐triazoles by the reaction of Hagemann's esters with tosyl azide in the presence of 20 mol‐% of proline as organocatalyst and DMSO as the solvent . After this seminal report, many enamine mediated triazole forming reactions were published, which utilize secondary amines such as proline, pyrrolidine, or diethylamine as the catalysts of choice . In general terms, the enolizable carbonyl compounds used in these reactions could be classified into three different categories according to the acidity of α‐H atoms: (1) activated saturated ketones 32a and 32b , (2) activated unsaturated carbonyl compounds, which include α,β‐unsaturated aldehydes 33 and Hagemann's esters 34 and (3) non‐activated ketones, for example, cyclic and acyclic ketones 35 (Scheme ).…”

Section: Organocatalytic Processes Involving Reactions Of Enaminesmentioning

confidence: 99%

The Rich Chemistry Resulting from the 1,3‐Dipolar Cycloaddition Reactions of Enamines and Azides

et al. 2017

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Enamines exhibit exceptionally high reactivity in their 1,3‐dipolar cycloaddition reactions with azides in comparison with other dipolarophiles. This review includes the reactions of various types of enamines with azides of different nature, including catalytic processes. The initial products of the reaction, 1,2,3‐triazolines, are generally unstable and very reactive compounds which are prone to undergo various ring transformations. This provides the background for new synthetic methods and novel reaction types. The formation of a variety of products derived from the reaction of enamines with azides such as mono‐, di‐and tri‐substituted 1,2,3‐triazoles, including N‐unsubstituted derivatives, fused, conjugated and spiro heterocycles, two types of amidines and diaminoalkenes are classified in this review according to the type of stabilization/transformation of the intermediate triazolines.

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Direct access to 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of allyl ketones with azides

Abstract: A general organocatalytic 1,3-dipolar cycloaddition reaction between allyl ketones and various azides is reported. The reaction is catalyzed by a secondary amine to generate substituted 1,2,3-triazoles with high levels of regioselectivity.

Cited by 105 publications

References 53 publications

Lewis Base Catalyzed Aerobic Oxidative Intermolecular Azide–Zwitterion Cycloaddition

Lewis Base Catalyzed Aerobic Oxidative Intermolecular Azide–Zwitterion Cycloaddition

1,2,3-Triazoles: Synthesis and Biological Application

The Rich Chemistry Resulting from the 1,3‐Dipolar Cycloaddition Reactions of Enamines and Azides

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