Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2‑Pyridone Alkaloids

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 cy...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (17), p.5203-5207
Main Authors: Angello, Nicholas H, Wiley, Robert E, Elmore, Tristan G, Perry, Ryan S, Scheerer, Jonathan R
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02145