- Highly c3-selective direct alkylation and arylation of 2-pyridones under visible-light-promoted photoredox catalysis
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An Ir photoredox catalyst-mediated highly site-selective direct alkylation and arylation of 2-pyridones has been developed. Under visible-light-promoted conditions, ethyl 2-bromo-2,2-difluoroacetate couples with various 2-pyridones exclusively at the C3 position. A similar photoredox catalysis is also effective for the direct C3- Arylation with diaryliodonium triflates. Thus, these reactions occurs under very mild conditions (blue LEDs irradiation and ambient temperature) to form the corresponding C3- Alkylated and arylated 2-pyridones of potential interest in medicinal and pharmaceutical chemistry.
- Najib, Atifah,Tabuchi, Sho,Hirano, Koji,Miura, Masahiro
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- Manganese-mediated C3-selective direct alkylation and arylation of 2-pyridones with diethyl malonates and arylboronic acids
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A manganese-mediated dehydrogenative direct alkylation of 2-pyridones with diethyl malonates has been developed. A similar reaction system is applicable to the direct arylation with arylboronic acids. These manganese-based reactions occur regioselectively at the C3 position of the 2-pyridones. The observed high C3 regioselectivity can complement precedented C-H functionalization protocols of the 2-pyridones in view of the site selectivity.
- Nakatani, Akihiro,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 1377 - 1385
(2014/03/21)
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- A convenient access to furo[3,2-c]pyridin-6(5H)-ones by the reaction of 5-iodo-4-methoxy-2-pyridones with terminal alkynes under microwave-enhanced Sonogashira conditions
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N-Alkyl-3-aryl-5-iodo-4-methoxypyridin-2(1H)-ones readily undergo sequential acetylide cross-coupling, demethylation, and furan annulation under classical Sonogashira reaction conditions to furnish 7-arylfuro[3,2-c]pyridin-4(5H)-ones, a class of hitherto
- Conreaux, David,Delaunay, Thierry,Desbordes, Philippe,Monteiro, Nuno,Balme, Geneviève
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experimental part
p. 3299 - 3301
(2009/08/09)
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- Novel 1,4-Dipolar Cycloaddition Reactions of 6-Oxo-6H-1,3-oxazin-3-ium-4-olates and of a 6-Oxo-6H-1,3-thiazin-3-ium-4-olate to Ketene Derivatives and Enamines
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The reactions of the ketene derivatives 4, 7, and 9 as well as of the enamines 13 and 17 with some selected title compounds are described.In these cases either primary adducts of type 5, 14, or 20 are produced by a 1,4-dipolar cycloaddition, or subsequent eliminations proceed with formation of products of type 8, 11, 16, or 18.The 2(1H)-pyridinones 8 are formed by thermolysis of 5, whereas 15a-d are accessible on treatment of 14a-d or 20 with acid.The observed regioselectivities are compared with the results of MNDO calculations and the FMO and PMO theory.
- Gotthardt, Hans,Flosbach, Carmen
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p. 951 - 960
(2007/10/02)
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