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Org Biomol Chem ; 20(7): 1453-1461, 2022 02 16.
Article En | MEDLINE | ID: mdl-35088800

The directing group assisted decarboxylative ortho-benzoylation of N-aryl-7-azaindoles with α-keto acids has been achieved by synergistic visible light promoted photoredox and palladium catalysis. The approach tenders rapid entry to aryl ketone architectures from simple α-keto acid precursors via the in situ generation of a benzoyl radical intermediate. The transformation provides a range of ortho-benzoylated N-aryl-7-azaindoles, with excellent site-selectivity and good functional group compatibility under mild reaction conditions. Biological target predictions indicate that these molecules may serve as potential anti-cancer and anti-viral agents.


Enzyme Inhibitors/chemistry , Indoles/chemistry , Palladium/chemistry , Catalysis , Decarboxylation , Enzyme Inhibitors/pharmacology , HIV Reverse Transcriptase/antagonists & inhibitors , HIV Reverse Transcriptase/metabolism , Humans , Indoles/pharmacology , Janus Kinase 3/antagonists & inhibitors , Janus Kinase 3/metabolism , Keto Acids/chemistry , Light , Molecular Structure , Oxidation-Reduction , Photochemical Processes , Proto-Oncogene Proteins c-pim-1/antagonists & inhibitors , Proto-Oncogene Proteins c-pim-1/metabolism , Tankyrases/antagonists & inhibitors , Tankyrases/metabolism
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