[Bmim]OH mediated Cu-catalyzed azide–alkyne cycloaddition reaction: A potential green route to 1,4-disubstituted 1,2,3-triazoles

Ali, Abdul Aziz; Konwar, Manashjyoti; Chetia, Mitali; Sarma, Diganta

doi:10.1016/j.tetlet.2016.11.014

Cited by 37 publications

(9 citation statements)

References 61 publications

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“…To explore the generality of the method, we apply this IL-based flow strategy to a chemocatalysis reaction, for example CuI-catalyzed azide–alkyne cycloaddition. , This reaction is an important route to access 1,4-disubstituted 1,2,3-triazoles (Figure A). In the batch system, it took 11 h to obtain 98.5% conversion of benzyl azide (Figure B).…”

Section: Resultsmentioning

confidence: 99%

Ionic Liquid Droplet Microreactor for Catalysis Reactions Not at Equilibrium

et al. 2017

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We develop a novel strategy to more effectively and controllably process continuous enzymatic or homogeneous catalysis reactions based on nonaqueous Pickering emulsions. A key element of this strategy is "bottom-up" construction of a macroscale continuous flow reaction system through packing catalyst-containing micron-sized ionic liquid (IL) droplet in oil in a column reactor. Due to the continuous influx of reactants into the droplet microreactors and the continuous release of products from the droplet microreactors, catalysis reactions in such a system can take place without limitations arising from establishment of the reaction equilibrium and catalyst separation, inherent in conventional batch reactions. As proof of the concept, enzymatic enantioselective trans-esterification and CuI-catalyzed cycloaddition reactions using this IL droplet-based flow system both exhibit 8 to 25-fold enhancement in catalysis efficiency compared to their batch counterparts, and a durability of at least 4000 h for the enantioselective trans-esterification of 1-phenylethyl alcohol, otherwise unattainable in their batch counterparts. We further establish a theoretical model for such a catalysis system working under nonequilibrium conditions, which not only supports the experimental results but also helps to predict reaction progress at a microscale level. Being operationally simple, efficient, and adaptive, this strategy provides an unprecedented platform for practical applications of enzymes and homogeneous catalysts even at a controllable level.

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Section: Resultsmentioning

confidence: 99%

Ionic Liquid Droplet Microreactor for Catalysis Reactions Not at Equilibrium

et al. 2017

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“…Many 1,2,3-triazole compounds are clinically important and exhibit various biologically important activities such as antibiotic 4 , anti- Human Immunodeficiency Virus drug 5 , anticancer 6 , antiviral 7 , etc . As a result, there is immense interest in the emerging synthetic protocols for these heterocycles 8 . Huisgen 1,3-dipolar azide/alkyne cycloaddition is the conventional method for 1,2,3-triazoles synthesis.…”

Section: Introductionmentioning

confidence: 99%

Catalytic activity and mechanistic investigation of 1D 2-Picolinic acid based Cu(II) coordination polymer in the selective construction of 1,4-disubstituted triazoles

Aier

Gayen

Пузари

2022

Sci Rep

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The catalytic activity of 1D 2-Picolinic acid based Cu (II) coordination polymer (CP1) in click reaction was evaluated to generate 1,4-disubstituted 1,2,3-triazoles selectively. The CP1 catalyst loading of 2 mol% was applied successfully in the reaction for primary azides with diverse functionalities of terminal alkynes in green solvent (EG/H2O). Moreover, the one-pot, multicomponent click reaction involving benzyl bromide, sodium azide, and phenylacetylene was also catalyzed by CP1. The findings show that 1D 2-Picolinic acid based Cu (II) coordination polymer catalytic systems are highly efficient for green click triazoles synthesis. DFT calculation supported the plausible mechanism involved in the CP1 catalyzed click reaction.

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“…Reactions like ring expansion of the diaziridine scaffold in monocyclic diaziridine derivatives and condensation reactions, such as the synthesis of aminothiadiazoles and dihydroisoquinolines, proceed with higher regio- and stereoselectivity in ILs compared to other organic solvents . It is worth mentioning that ILs have served as efficient reaction media for the synthesis of 1,5-disubstituted as well as 1,4-disubstituted-1,2,3-triazoles …”

Section: Introductionmentioning

confidence: 99%

A Simple Work-Up-free, Solvent-free Approach to Novel Amino Acid Linked 1,4-Disubstituted 1,2,3-Triazoles as Potent Antituberculosis Agents

Garg

Borah²,

Trivedi

et al. 2020

ACS Omega

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An efficient, green strategy for synthesis of 1,4-disubstituted-1,2,3-triazole has been developed using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) acetate ionic liquid (200 μL) under a solvent- and external base-free condition. This protocol is further applied for the synthesis of novel amino acid containing 1,2,3-triazole molecules, which were then evaluated for potential antitubercular and antibacterial activities. Cytotoxicity assay of the compounds was also performed. In silico analysis of the promising compounds selected through experimental analysis was thereafter performed for visualizing molecular interactions and predicting binding affinities between our synthesized molecules, which exhibited good activity in experimental studies and the DprE1 target protein of Mycobacterium tuberculosis. Durg-likeness studies also show potential of the synthesized molecules as drug candidates.

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[Bmim]OH mediated Cu-catalyzed azide–alkyne cycloaddition reaction: A potential green route to 1,4-disubstituted 1,2,3-triazoles

Cited by 37 publications

References 61 publications

Ionic Liquid Droplet Microreactor for Catalysis Reactions Not at Equilibrium

Ionic Liquid Droplet Microreactor for Catalysis Reactions Not at Equilibrium

Catalytic activity and mechanistic investigation of 1D 2-Picolinic acid based Cu(II) coordination polymer in the selective construction of 1,4-disubstituted triazoles

A Simple Work-Up-free, Solvent-free Approach to Novel Amino Acid Linked 1,4-Disubstituted 1,2,3-Triazoles as Potent Antituberculosis Agents

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