Cu(II)-assisted oxidation of quinoline-2-carbaldehyde hydrazone to give [1,2,3]triazolo[1,5-α]quinoline: The first example of Cu(I) complex containing [1,2,3]triazolo-ligand

Abstract:The copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click chemistry") was studied employing copper-in-charcoal (Cu/C) and a variety of copper metal sources as "heterogeneous" catalysts. The type and pretreatment conditions of the different copper sources on the CuAAC were investigated. In addition, the effect of copper leaching from the catalyst over time and in dependence on the reaction mixture composition was studied by ICP-MS analysis in the continuous flow mode. These investigations confirm a "homogeneous" mechanism and suggest surface layer copper(I) oxide as the catalytically active species in CuAAC chemistry involving zerovalent copper metal.

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Mechanistic Insights into Copper(I)‐Catalyzed Azide‐Alkyne Cycloadditions using Continuous Flow Conditions

Fuchs

et al. 2010

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Progress on Pyridotriazole Chemistry: Synthesis and Transformations

Shen

Yin

et al. 2022

Asian J Org Chem

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Pyridotriazoles are an important subclass of azacyclic compounds. Although known in early 1950s, these compounds aroused little attention in synthetic chemistry for a long time. This situation has changed during the past years as ever-increasing recognitions on their rich properties and reactivities. Particularly, the recent exploration on their potentials as carbene or metal carbene precursors in denitrogenative transformations catalytically or non-catalytically has met considerable success. A lot of new synthetic approaches towards azacyclic compounds such as indolizines, imidazopyridines, pyridoisoquinolinones and pyridoindoles as well as a wide range of functionalized pyridines have been established based on the transformations of pyridotriazoles. Meanwhile, a considerable number of new reactions are developed for the synthesis of pyridotriazoles. In particular, the development of new transition-metal catalyzed tandem reactions has enabled selective generation of diverse pyridotriazoles in efficient manners from simple starting materials. This review surveys main advances in this field over the last two decades and aims to provide an up-to-date overview on the knowledge of pyridotriazole chemistry.

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Facile One‐Pot Synthesis of [1, 2, 3]Triazolo[1, 5‐a]Pyridines from 2‐Acylpyridines by Copper(II)‐Catalyzed Oxidative NN Bond Formation

Hirayama

Ueda

Okada

et al. 2014

Chemistry A European J

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An efficient and simple method for the synthesis of various [1, 2, 3]triazolo[1, 5-a]pyridines has been established. The method involves a copper(II)-catalyzed oxidative N-N bond formation that uses atmospheric oxygen as the terminal oxidant following hydrazonation in one pot. The use of ethyl acetate as the solvent dramatically promotes the oxidative N-N bond-formation reaction and enables the application of oxidative cyclization in the efficient one-pot reaction. A mechanism for the reaction was proposed on the basis of the results of a spectroscopic study.

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Cu(II)-assisted oxidation of quinoline-2-carbaldehyde hydrazone to give [1,2,3]triazolo[1,5-α]quinoline: The first example of Cu(I) complex containing [1,2,3]triazolo-ligand

Cited by 35 publications

References 19 publications

Mechanistic Insights into Copper(I)‐Catalyzed Azide‐Alkyne Cycloadditions using Continuous Flow Conditions

Mechanistic Insights into Copper(I)‐Catalyzed Azide‐Alkyne Cycloadditions using Continuous Flow Conditions

Progress on Pyridotriazole Chemistry: Synthesis and Transformations

Facile One‐Pot Synthesis of [1, 2, 3]Triazolo[1, 5‐a]Pyridines from 2‐Acylpyridines by Copper(II)‐Catalyzed Oxidative NN Bond Formation

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