Nitrogen heterocycles, especially polycyclic compounds, are significant skeletons in valuable molecules. Herein, we developed an efficient and practical visible-light-induced acylation/cyclization of active alkenes with acyl oxime derivatives for constructing acylated indolo/benzimidazo-[2,1,]isoquinolin-6(5) ones. This reaction was compatible with various functional groups and a series of fused indole/imidazole skeletons were prepared in up to 95% yield at room temperature.
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http://dx.doi.org/10.1039/d2ob00528j | DOI Listing |
J Org Chem
August 2024
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
A visible-light-induced radical cascade regioselective acylation/cyclization of 1,7-dienes with acyl oxime esters for the preparation of acylation polycyclic compounds via NCR-mediated C-C σ-bond cleavage is established. The transformation involves the cleavage of the C-C σ-bond in acyl oxime esters and selective addition of the electron neutral C═C bonds in 1,7-dienes for the synthesis of acyl polycyclic quinolinone derivatives, not the traditional seven-membered ring products. The strategy offers several advantages, including broad substrate tolerance, no need for bases, hyperstoichiometric radical initiators, and other auxiliaries.
View Article and Find Full Text PDFOrg Biomol Chem
May 2022
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
Nitrogen heterocycles, especially polycyclic compounds, are significant skeletons in valuable molecules. Herein, we developed an efficient and practical visible-light-induced acylation/cyclization of active alkenes with acyl oxime derivatives for constructing acylated indolo/benzimidazo-[2,1,]isoquinolin-6(5) ones. This reaction was compatible with various functional groups and a series of fused indole/imidazole skeletons were prepared in up to 95% yield at room temperature.
View Article and Find Full Text PDFOrg Biomol Chem
October 2021
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
A nitrogen-centered radical-mediated carbon-carbon bond cleavage strategy is described to synthesize functionalized 3-acylcoumarins. The strategy is enabled by the visible-light-induced acylation/cyclization of alkynoates with various acyl oxime compounds in acetonitrile. The difunctionalization of carbon-carbon triple bonds precedes the generation of iminyl radicals, which is followed by the formation of acyl radicals.
View Article and Find Full Text PDFJ Org Chem
October 2021
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
A convenient and efficient visible-light-induced tandem acylation/cyclization of -propargylindoles with aryl- or alkyl-substituted acyl oxime esters for the synthesis of 2-acyl-substituted 9-pyrrolo[1,2-]indoles under transition-metal-free conditions, which proceeds nitrogen-centered radical-mediated cleavage of the C-C σ-bond in acyl oxime esters, is established. The aryl or alkyl acyl radicals, which come from acyl oxime esters, attack the C-C triple bonds in -propargylindoles and then go through intramolecular cyclization/isomerization.
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