Sequencing [3+2]-cycloaddition and multicomponent reactions: A regioselective microwave-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles using ionic liquid supported Cu(II) precatalysts in methanol

Saikia, Ananya Anubhav; Rao, R. Nishanth; Das, Soumyadip; Jena, Sushovan; Rej, Sourav; Maiti, B. R.; Chanda, Kaushik

doi:10.1016/j.tetlet.2020.152273

Cited by 38 publications

(24 citation statements)

References 54 publications

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“…The combination of alkyl halides [27a–f] with NaN 3 in the presence of terminal alkynes and copper catalyst would accomplish the tandem synthesis of 1,4‐disubstituted 1,2,3‐triazoles 27.1 . Compared with applications of aryl halides in similar azidation and 1,3‐dipolar cycloaddition, alkyl halides performed much better.…”

Section: Synthesis Of Triazolesmentioning

confidence: 99%

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Decade Advances of NaN₃ in Three‐component Reactions

Wang

et al. 2023

Asian J Org Chem

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Decade advances of sodium azide (2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020)(2021)(2022) have been summarized via mechanisms and target products. Sodium azide is commonly used as a nucleophile (N 3 À ) or radical source ( * N 3 ) in three-component reactions. It's reac-tions with alkenes, alkynes, RÀ X (X=F, Cl, Br, I, OTs, B(OH) 2 , BF 3 K, I + ArO À Tf, N 2 + O À SO 3 -SiO 2 ) and other electrophiles will be discussed.

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Section: Synthesis Of Triazolesmentioning

confidence: 99%

“…Different kinds of copper catalysts have been proved to be efficient. High yields of 1,2,3‐triazoles were cleanly synthesized in water [27a,b,f] or MeOH [27c,e] . The Bosc group [27g] studied the nickel‐catalyzed synthesis of 1,5‐disubstituted 1,2,3‐triazoles 27.2 (Scheme 27).…”

Section: Synthesis Of Triazolesmentioning

confidence: 99%

Decade Advances of NaN₃ in Three‐component Reactions

Wang

et al. 2023

Asian J Org Chem

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“…Substituted benzyl bromide bearing an electron-donating group interacted favorably, resulting in high yields of the corresponding triazoles. Likewise, slow reaction rates were seen when similar triazoles were prepared from benzyl bromides or substituted benzyl bromides bearing electron withdrawing groups . This methodology was further extended to the synthesis of rufinamide, an antiepileptic drug.…”

Section: Synthesis Of Cu-catalyzed Heterocyclic Moieties Via Microwav...mentioning

confidence: 99%

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

Jena

Chanda

2023

ACS Omega

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Heterocyclic moieties play a significant role in the field of drug discovery. C−N and C−O bond formation reactions are the primary synthetic sequence for the generation of heterocyclic molecules. The generation of C−N and C−O bonds involves the use of mostly Pd or Cu catalysts although other transition metal catalyst's are also involved. However, in C−N and C−O bond formation reactions, several problems were faced such as catalytic systems containing costly ligands, lack of substrate scope, lots of waste generation, and high temperature conditions. So it is imperative to uncover new eco-friendly synthetic strategies. In view of enormous drawbacks, it is important to develop an alternate microwave-assisted synthesis of heterocycles via C−N and C−O bond formation, which provides a short reaction time, tolerance for functional groups, and less waste production. Numerous chemical reactions have been accelerated using microwave irradiation which provides a cleaner reaction profile, lower energy consumption, and higher yields. This review article highlights a comprehensive overview on the potential application of microwave assisted synthetic routes for the synthesis of diverse heterocycles via mechanistic pathways covering the year ranges from 2014 to 2023, along with possible biological interests.

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“…The direct formation of Runamide by the CuAAC reaction between 2,6-diuorobenzyl azide and propiolamide in batch has been reported using various conditions and catalysts. [48][49][50][51] Its synthesis under ow conditions from propiolamide, formed inline from ethyl propiolate, using copper tubing was reported by Jamison et al 52 with 92% yield and 20 : 1 1,4-to 1,5regioselectivity.…”

Section: Synthesis Of Api As An Application Examplementioning

confidence: 99%