A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

Javaherian, Mohammad; Kazemi, Foad; Ghaemi, Masoumeh

doi:10.1016/j.cclet.2014.09.005

Cited by 19 publications

(8 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Since 2015, several researchers reported the applicability of ionic liquids (ILs) as a solvent and catalyst for the regioselective synthesis of 1,2,3-triazoles. The use of ILs as nontoxic benign solvents can improve the reaction rate and regioselectivity of the cycloaddition reaction ( Javaherian et al, 2014 ). A simple bifunctional IL catalyst, namely, choline chloride-CuCl was found highly active for the [3 + 2] Huisgen cycloaddition in H 2 O ( Liu et al, 2016 ).…”

Section: Synthetic Approachesmentioning

confidence: 99%

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Matin

Chakraborty

Rahman

et al. 2022

Front. Mol. Biosci.

141

View full text Add to dashboard Cite

Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Structurally, there are two types of five-membered triazoles: 1,2,3-triazole and 1,2,4-triazole. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities. These are also important in organocatalysis, agrochemicals, and materials science. Thus, they have a broad range of therapeutic applications with ever-widening future scope across scientific disciplines. However, adverse events such as hepatotoxicity and hormonal problems lead to a careful revision of the azole family to obtain higher efficacy with minimum side effects. This review focuses on the structural features, synthesis, and notable therapeutic applications of triazoles and related compounds.

show abstract

Section: Synthetic Approachesmentioning

confidence: 99%

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Matin

Chakraborty

Rahman

et al. 2022

Front. Mol. Biosci.

141

View full text Add to dashboard Cite

show abstract

“…"Click" chemistry refers to a type of catalyst-free reactions with solvent and functional groups tolerance under mild conditions, which have spurred much attention on a wide range of research elds since it was conceptually put forward for the rst time by Sharpless in 2001. [1][2][3][4][5] Apart from the well-known CuAAC reaction [6][7] and metal-free dipolar cycloadditions, [8][9] the thiol-based click reactions (e.g. thiol-ene/yne, [10][11] thiol-epoxy, [12] thiol-isocyanate [13] and thiol-Michael addition reaction [14] ) have been extensively implemented in realms of organic synthesis, [15] surface functionalization, [16] polymer modi cation, [17][18][19] and especially, bio-conjugations, [20] due to the fast reaction rate and wide presented thiol groups in natural amino acid residues.…”

Section: Introductionmentioning

confidence: 99%

Atom-economic and Self-reported Thiol Activation through Visible Light Induced Photo-rearrangment for Efficient Click-ligation

Zhang

Deng

et al. 2022

Preprint

View full text Add to dashboard Cite

Photo-induced thiol release offers great opportunities for spatial/temporal regulation over selectivity and efficiency of thiol-ene ligations. Conventional means mainly count on photo-caged thiol precursors design, which may inevitably produce fragmented “wastes” during photo-activation and possibly turn on a series of undesirable side reactions. Additionally, the commonly used light sources (< 450 nm) remarkably restrict the potential bio-applications because of bio-toxicity and limited tissue penetration. To tackle these setbacks, we presented herein a novel family of photo-responsive 2-methylthiophene/benzo[b]thiophene perylene bisimides that generated free thiols with green light (λ = 530 nm) via a “waste-free” photo-rearrangement mechanism. The in situ photo-unmasked thiols thus enabled a subsequent Michael addition with electron-deficient substrates (e.g., maleimide). By virtue of the intrinsic fluorescence evolution from the rearrangement of perylene bisimides scaffold, the whole process of thiol formation could be self-reported, potentiating this newly-exploited, visible-light-initiated click system for future applications in biomaterials fabrication and in vivo bio-conjugation/bio-labelling.

show abstract

“…To synthesize 1,2,3‐triazole derivatives, the copper‐catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most attractive and important reaction in nature and synthetic organic chemistry . Copper‐containing nanoparticles have recently emerged as effective catalysts in the 1,3‐dipolar azide–alkyne cycloaddition reactions …”

Section: Introductionmentioning

confidence: 99%

Synthesis of copper nanoparticles supported on MoO₃ using Sun spurge leaf extract and their catalytic activity

Janmohammadi

Amini

Sabaghnia

et al. 2018

Applied Organom Chemis

View full text Add to dashboard Cite

Copper nanoparticles supported on MoO 3 (Cu NPs/MoO 3 ) were prepared by a green method using Sun spurge leaf extract. Cu NPs/MoO 3 nanoparticles were characterized by X-ray diffraction analysis, energy dispersive X-ray analysis, scanning electron microscope and transmission electron microscope. The catalytic activity of this well-defined material in three-component CuAAC reactions was tested to produce 1,4-disubstituted-1,2,3-triazoles in good to excellent yields in water as a green solvent. More importantly, the catalyst can be recovered and reused efficiently up to five consecutive cycles with no significant loss of catalytic activity.

show abstract

A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

Cited by 19 publications

References 25 publications

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Atom-economic and Self-reported Thiol Activation through Visible Light Induced Photo-rearrangment for Efficient Click-ligation

Synthesis of copper nanoparticles supported on MoO₃ using Sun spurge leaf extract and their catalytic activity

Contact Info

Product

Resources

About

A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

Cited by 19 publications

References 25 publications

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Atom-economic and Self-reported Thiol Activation through Visible Light Induced Photo-rearrangment for Efficient Click-ligation

Synthesis of copper nanoparticles supported on MoO3 using Sun spurge leaf extract and their catalytic activity

Contact Info

Product

Resources

About

Synthesis of copper nanoparticles supported on MoO₃ using Sun spurge leaf extract and their catalytic activity