Substituent effect on selectivity in photoisomerization of 4-pyrones and 4-pyridones

The photochemical cycloaddition is highly regioselective. For preparative purposes, the ring junction can be equilibrated to the thermodynamically more stable &-junction. Only the 'endo'/ 'exo' selectivity at the C-atom bearing the olefin substituent cannot be controlled. The photodimerization of 12 is the only side reaction. Using a slight excess of the olefin, the photodimerization can be suppressed. The protecting group at the N-atom of the dihydropyridinone can be varied in order to introduce an internal sensitizer, as shown with 1-acyl-substituted compound 29, which underwent the cycloaddition process even with sunlight.Einleitung. -Die photochemischen [2 + 21-Cycloadditionen an a$-ungesattigte Cy-

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Photochemical methoxy/hydroxymethyl rearrangement in 3‐methoxy‐N‐substituted‐4‐pyriclones

Stiplošek

Šindler‐Kulyk

Jakopcic

et al. 1989

Journal of Heterocyclic Chem

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Substituent effect on selectivity in photoisomerization of 4-pyrones and 4-pyridones

Cited by 11 publications

References 9 publications

ChemInform Abstract: SUBSTITUENT EFFECT ON SELECTIVITY IN PHOTOISOMERIZATION OF 4‐PYRONES AND 4‐PYRIDONES

ChemInform Abstract: SUBSTITUENT EFFECT ON SELECTIVITY IN PHOTOISOMERIZATION OF 4‐PYRONES AND 4‐PYRIDONES

1‐Methoxycarbonyl‐substituiertes 2,3‐Dihydropyridin‐4(1H)‐on (= Methyl‐1,2,3,4‐tetrahydro‐4‐oxopyridin‐1‐carboxylat) als Chromophor für die photochemische [2 + 2]‐Cycloaddition

Photochemical methoxy/hydroxymethyl rearrangement in 3‐methoxy‐N‐substituted‐4‐pyriclones

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