ArticleChemistry & biodiversity2022
Cu-Catalyzed Chan-Evans-Lam Coupling Reactions of 2-Nitroimidazole with Aryl Boronic Acids: An Effort toward New Bioactive Agents against S. pneumoniae.
Article in Chemistry & biodiversity, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 11 citations in OpenAlex.
- Copper(II) NHC pincer complexes containing 1,2,3-triazole units: Synthesis, structure and catalysis for C─N bond forming reactions.Tetrahedron letters · 2025Article
- Pd-, Cu-, and Ni-Catalyzed Reactions: A Comprehensive Review of the Efficient Approaches towards the Synthesis of Antibacterial Molecules.Pharmaceuticals (Basel, Switzerland) · 2024Review
- Aminoquinoline-Based Tridentate (Molecules (Basel, Switzerland) · 2024Article
- Copper complexes for the chemoselectiveDalton transactions (Cambridge, England : 2003) · 2023Article
- Cu-NHC Complex for Chan-Evans-Lam Cross-Coupling Reactions ofEuropean journal of organic chemistry · 2023Article
- Cu-Catalyzed Cross-Coupling Reactions of Enamines and Terminal Alkynes: Access of Propargylamines as Neurodegenerative Disorder Agents.Asian journal of organic chemistry · 2023Article
- Sodium Trifluoroacetate mediated Copper-CatalyzedTetrahedron letters · 2023Article
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
The coupling of phenylboronic acids with poorly-activated imidazoles is studied as a model system to explore the use of copper-catalyzed Chan-Evans-Lam (CEL) coupling for targeted C-N bond forming reactions. Optimized CEL reaction conditions are reported for four phenanthroline-based ligand systems, where the ligand 4,5-diazafluoren-9-one (dafo, L2) with 1 molar equivalent of potassium carbonate yielded the highest reactivity. The substrate 2-nitroimidazole (also known as azomycin) has documented antimicrobial activity against a range of microbes. Here N-arylation of 2-nitroimidazole with a range of aryl boronic acids has been successfully developed by copper(II)-catalyzed CEL reactions. Azomycin and a range of newly arylated azomycin derivatives were screened against S. pneumoniae, where 1-(4-(benzyloxy)phenyl)-2-nitro-1H-imidazole (3d) was demonstrated to have a minimal inhibition concentration value of 3.3 μg/mL.
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