3,4-and 3,5-disubstituted 2-pyridones using an intermolecular cycloaddition/cycloreversion strategy: toward the synthesis of aristopyridinone A

Authors

Maren K. Leibowitz, William & Mary
Ethan S. Winter, William & Mary
Jonathan R. Scheerer, William & Mary

Document Type

Article

Department/Program

Chemistry

Journal Title

Tetrahedron Letters

Pub Date

2015

Volume

56

Issue

44

First Page

6069

Abstract

The intermolecular cycloaddition of pyrazinone precursors with alkyne substrates was evaluated. The resulting regioisomeric [2.2.2]-diketopiperazine alkene cycloadducts were diverted into 2-pyridone products through cycloreversion of the [2.2.2]-bicyclic intermediates. New insights into the regioselectivity of pyrazinone azadiene Diels-Alder reactions as well as cycloreversion reactivity were revealed in this study. Synthetic sequences using this [4+2]/r[4+2] strategy were determined that can produce predominantly the 3,5-disubstituted 2-pyridone alkaloid structures; pyridones featuring the 3,4-substitution pattern are observed as the minor regioisomeric products. (C) 2015 Elsevier Ltd. All rights reserved.

Recommended Citation

Leibowitz, Maren K.; Winter, Ethan S.; and Scheerer, Jonathan R., 3,4-and 3,5-disubstituted 2-pyridones using an intermolecular cycloaddition/cycloreversion strategy: toward the synthesis of aristopyridinone A (2015). Tetrahedron Letters, 56(44), 6069-6072.
10.1016/j.tetlet.2015.09.067

DOI

10.1016/j.tetlet.2015.09.067