The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization.

Max Van Hoof, Santhini Pulikkal Veettil, Wim Dehaen

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

3 authors.

Max Van HoofMolecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium.ORCID 0000-0001-5396-9892

Santhini Pulikkal VeettilMolecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium.

Wim DehaenMolecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium.ORCID 0000-0002-9597-0629

Funding

KU Leuven C14/19/78

6 · The paper itself

Abstract

4-Sulfonyl-1,2,3-triazole scaffolds possess promising bioactivities and applications as anion binders. However, these structures remain relatively unexplored and efficient synthetic procedures for their synthesis remain desirable. A practical room-temperature, aerobic copper-catalyzed three-component reaction of aromatic ketones, sodium sulfinates, and azides is reported. This procedure allows for facile access to 4-sulfonyl-1,5-disubstituted-1,2,3-triazoles in yields ranging from 34 to 89%. The reaction proceeds via a sequential aerobic copper(II)chloride-catalyzed oxidative sulfonylation and the Dimroth azide-enolate cycloaddition.

Indexed as

Anti-Infective AgentsCatalysisChemistry Techniques, SyntheticCopperCyclizationHumansMolecular StructureOxidation-ReductionOxygenPregnane X ReceptorProteinase Inhibitory Proteins, SecretorySulfinic AcidsTriazolesAnti-Infective AgentsCopperNR1I2 protein, humanOxygenPregnane X ReceptorProteinase Inhibitory Proteins, SecretorySulfinic AcidsTriazoles4-sulfonyl-1,2,3-triazolesaerobic oxidationC-H activationcopper-catalysisDimroth azide–enolate cyclizationthree-component tandem reaction

Identifiers

PMID33499353

DOI10.3390/molecules26030581

PMCPMC7865689

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.