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

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2018 Aug 11

PMID 30095269

Citations 1

Authors

Nicholas H Angello

Robert E Wiley

Tristan G Elmore

Ryan S Perry

Jonathan R Scheerer

Affiliations

Soon will be listed here.

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.

Citing Articles

Synthesis and Spectrophotometric Analysis of 1-Azafluorenone Derivatives.

Angello N, Wiley R, Abelt C, Scheerer J Molecules. 2020; 25(15).

PMID: 32722081 PMC: 7436005. DOI: 10.3390/molecules25153358.

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