A new domino reaction sequence for the construction of 2-pyridone structures is reported. The reaction sequence begins with diacetyldiketopiperazine and proceeds via aldol condensation, alkene isomerization, and intramolecular Diels-Alder cycloaddition. The intermediate [2.2.2]diazabicycloalkene cycloadducts can be isolated or can engage in a base-accelerated extrusion of one lactam bridge to provide the 2-pyridone cycloreversion products. The operation leading to pyridone products can occur in one reaction vessel and proceeds at convenient temperatures.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6220673 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.8b02145 | DOI Listing |
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