Synthesis of 2‐(1,2,3‐Triazolyl)benzamide Derivatives by a Copper(I)‐Catalyzed Multicomponent Reaction

Hayeebueraheng, Abdulhakim; Kaewmee, Benyapa; Rukachaisirikul, Vatcharin; Kaeobamrung, Juthanat

doi:10.1002/ejoc.201701316

Cited by 8 publications

(4 citation statements)

References 47 publications

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“…Hayeebueraheng and coauthors described the multicomponent synthesis of 2-(1,2,3triazolyl)benzamides 23 starting from 2-iodobenzamides 22, sodium azide, and terminal alkynes 5 leading to 20 examples in 60-96% yield (Scheme 11) [65]. This copper(I)-catalyzed one-step cycloaddition only proceeds in the absence of a base and proceeds quite rapidly.…”

Section: Triazolesmentioning

confidence: 99%

Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

Niedballa

Müller

2022

Catalysts

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Multicomponent processes are beneficial tools for the synthesis of heterocycles. As densely substituted bifunctional electrophiles, ynones are essential intermediates by applying cyclocondensations or cycloadditions in numerous heterocycle syntheses. The respective alkynoyl intermediates are generally accessible by palladium-, copper- and palladium/copper-catalyzed alkynylation. In turn, the mild reaction conditions allow for a fast and versatile entry to functional heterocycles in the sense of consecutive multicomponent processes. This review collates and presents recent advances in accessing thirteen heterocycle classes and their applications by virtue of catalytic alkynoyl generation in diversity-oriented multicomponent syntheses in a one-pot fashion.

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Section: Triazolesmentioning

confidence: 99%

Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

Niedballa

Müller

2022

Catalysts

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“…[ 38 ] In 2017, Kaeobamrung's group reported an intermolecular domino C‐N coupling/azide alkyne cycloaddition reaction of 2‐iodobenzamides 42 , terminal alkynes 43 , and NaN 3 , which was promoted by a copper catalyst in situ generated from CuBr and L ‐proline (Scheme 9). [ 39 ] This reaction provided the desired products in excellent yields, but only iodobenzamides were suitable for the reaction. By performed in DMSO at 90 °C, the transformation provided the corresponding product 2‐(1,2,3‐triazolyl)benzamide 44a in 82% yield, but no product was observed without L ‐proline.…”

Section: L‐proline‐assisted Copper‐catalyzed Cascade Reactionsmentioning

confidence: 99%

The synthesis ofN‐containing heterocyclic compounds catalyzed by copper/L‐proline

2020

Applied Organom Chemis

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N‐containing heterocyclic compounds are one of the most important motifs prevalent in various bioactive natural products and pharmaceuticals. Given the significance of N‐containing heterocyclic compounds, various synthetic strategies have been developed. Copper/ligand (abbreviated as [CuL])‐catalyzed cascade reaction is a powerful and efficient tool for the construction of N‐containing heterocyclic compounds. L‐proline is one universal ligand and has been utilized in the copper‐catalyzed reactions. In this review, copper/L‐proline‐catalyzed tandem reaction to synthesize the five‐ and six‐membered compounds is emphatically introduced. By comparing the yields in the presence and absence of the ligand, the importance of L‐proline is recorded. Moreover, the function of L‐proline is expounded on the basis of the reaction mechanism from original article.

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“…Cu‐catalysed one‐pot multicomponent click reaction has been used under mild conditions for the synthesis of 2‐(1,2,3,‐triazolyl)benzamides from 2‐iodobenzamides, NaN 3 and terminal alkynes (Scheme ) . The reaction involves C(aryl)‐N bond formation and azide‐alkyne cycloaddition (CuAAC).…”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

“…Generally MCRs are classified in to three main categories (i) Sequential reactions (ii) Domino−type reactions and (iii) Consecutive reactions . MCRs also incorporate unstable reactive intermediates . This protocol is advantageous since heterocycles could be synthesised using fewer steps when compared with classical synthesis routes .…”

Section: Introductionmentioning

confidence: 99%

Copper‐Catalysed Multicomponent Syntheses of Heterocycles

Cherian¹,

Harry²,

Saranya³

et al. 2019

Asian J Org Chem

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Heterocycles cover a wide range of organic compounds and are ubiquitous in different areas of life sciences and technology. Multicomponent syntheses of heterocycles are very advantageous in comparison with the classical methods of heterocycle synthesis. In this review, copper-catalysed multicomponent reactions used for the synthesis of heterocycles published between 2004 and 2018 are summarised.[a] R. Scheme 1. Synthesis of 2-iminooxetanes and maleimides by Cu-catalysed three-component reaction and ring expansion respectively.

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Synthesis of 2‐(1,2,3‐Triazolyl)benzamide Derivatives by a Copper(I)‐Catalyzed Multicomponent Reaction

Cited by 8 publications

References 47 publications

Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

The synthesis ofN‐containing heterocyclic compounds catalyzed by copper/L‐proline

Copper‐Catalysed Multicomponent Syntheses of Heterocycles

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