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The Chemistry of 6-Dialkylamino-2H-1,3-oxazin-2-ones. Reversible Thermal Ring-opening and Cycloaddition Reactions with N-Arylmaleimides and 1-Diethylaminopropyne. X-Ray Crystal Structures of a 5H-2-Pyridone and a 1H-2-Pyridone

DOI: 10.1039/P19810002878

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2878 - 2883 (1981)

Update date:2022-08-05

Topics:

Authors:

Baydar, Ahmet E.Baydar, Ahmet E.

Boyd, Gerhard V.Boyd, Gerhard V.

Lindley, Peter F.Lindley, Peter F.

Watson, FrankWatson, Frank

Manley, Paul W.Manley, Paul W.

Storr, Richard C.Storr, Richard C.

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Article abstract of DOI:10.1039/P19810002878

Flash-vacuum pyrolysis of the 1,3-oxazin-2-ones (1) and (9) gave the valence-isomeric carbamoylvinyl isocyanates (8) and (10), respectively, which recyclised to the oxazinones at room temperature.The oxazinones reacted with N-arylmaleimides in a Diels-Alder fashion; with 1-diethylaminopropyne, however, the first oxazinone yielded the isomeric pyridones (17) and (21), whose structures were determined by X-ray analysis.

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