Pyrazine chemistry. Part V. Diels-Alder reactions of some 2,5-dihydroxypyrazines
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 404-409
- https://doi.org/10.1039/p19730000404
Abstract
Certain 2,5-dihydroxypyrazines and related systems undergo 1,4-cycloaddition reactions. Dimethyl acetylenedicarboxylate reacts to give bicyclic adducts which readily undergo a retro-Diels-Alder reaction with elimination of cyanic acid and formation of substituted pyridones. 5-Ethoxy-1,3-dimethylpyrazin-2-one (16) has been synthesised and shown to undergo ready cycloaddition reactions even with non-activated double bonds. The implications of these reactions relative to the biosynthesis of the mould metabolite brevianamide A and related compounds are discussed.Keywords
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