Solid-Phase Synthesis of Pyridones and Pyridopyrazines as Peptidomimetic Scaffolds

We report the syntheses of peptidomimetic opioids containing the core structure N-alkyl-2-alkyl-2,3-dihydro-4-pyridone. By employing imines bound on a solid support and the Danishefsky diene, this [4 + 2] cyclocondensation reaction facilitates the synthesis of novel complex heterocycles. The central...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 1999-11, Vol.1 (9), p.1407-1409
Main Authors: Creighton, Christopher J, Zapf, Christoph W, Bu, Jane H, Goodman, Murray
Format: Article
Language:English
Subjects:
Molecular Mimicry
Peptides - chemistry
Pyrazines - chemistry
Pyridones - chemical synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We report the syntheses of peptidomimetic opioids containing the core structure N-alkyl-2-alkyl-2,3-dihydro-4-pyridone. By employing imines bound on a solid support and the Danishefsky diene, this [4 + 2] cyclocondensation reaction facilitates the synthesis of novel complex heterocycles. The central reaction is carried out under mild conditions and employs readily available building blocks. In this study we demonstrate the suitability of N-alkyl-2-alkyl-2,3-dihydro-4-pyridones as a central scaffold for peptidomimetics and establish the scope of this [4 + 2] cyclocondensation reaction with imino acids on a solid phase. We also combine the synthesis of diketopiperazines with the [4 + 2] cyclocondensation reaction to form a 9,9a-dihydro-2H-pyrido-[1,2a]-pyrazine-3,8(1,4-dialkyl)dione, a bicyclic molecule containing a pyridopyrazine core structure.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990960u