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A practical flow synthesis of 1,2,3-triazoles† † Electronic supplementary information (ESI) available. See https://doi.org/10.1039/d2ra04727f

ABSTRACT: A robust and versatile protocol for synthesis of 1-monosubstituted and 1,4-disubstituted 1H-1,2,3-triazoles was established under continuous flow conditions using copper-on-charcoal as a heterogeneous catalyst. This methodology allowed for the synthesis of a diverse set of substituted 1,2,3-triazoles with good functional group tolerance and high yields. 2-Ynoic acids were also used as small-chain alkyne donors in a decarboxylation/cycloaddition cascade, allowing gaseous reagents to be bypassed, delivering desired triazoles in high yields. The developed methodology was used to synthesize an antiepileptic agent, rufinamide, which was obtained in 96% isolated yield. Copper-on-charcoal is an excellent heterogeneous catalyst for the alkyne–azide cycloaddition reaction performed under continuous flow conditions. 2-Ynoic acids undergo decarboxylation/cycloaddition cascade giving triazoles bearing small alkyl chains.

SUBMITTER: Drelinkiewicz D

PROVIDER: S-EPMC9551675 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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