Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids.
Org Lett
; 20(17): 5203-5207, 2018 09 07.
Article
em En
| MEDLINE
| ID: mdl-30095269
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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Piridonas
/
Alcaloides
/
Alcenos
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article