Work

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

Year: 2018

Type: article

Abstract: 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.8b02145

Authors: Nicholas H. Angello, Robert E. Wiley, Tristan G. Elmore, Ryan S. Perry, Jonathan R. Scheerer

Institution: William & Mary

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Award: New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridines