Convergent and rapid assembly of substituted 2-pyridones through formation of N-alkenyl alkynylamides followed by gold-catalyzed cycloisomerization

Hidetomo Imase; Keiichi Noguchi; Masao Hirano; Ken Tanaka

doi:10.1021/ol801466f

Convergent and rapid assembly of substituted 2-pyridones through formation of N-alkenyl alkynylamides followed by gold-catalyzed cycloisomerization

Org Lett. 2008 Aug 21;10(16):3563-6. doi: 10.1021/ol801466f. Epub 2008 Jul 18.

Authors

Hidetomo Imase¹, Keiichi Noguchi, Masao Hirano, Ken Tanaka

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, and Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.

PMID: 18636742
DOI: 10.1021/ol801466f

Abstract

A new method for the convergent and rapid assembly of substituted 2-pyridones was developed through the formation of N-alkenyl alkynylamides (amide-linked 1,5-enynes) by N-acylation of imines with alkynoyl chlorides and the subsequent cationic Au(I)/PPh 3-catalyzed cycloisomerization.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Alkynes / chemistry*
Amides / chemical synthesis*
Amides / chemistry
Catalysis
Cyclization
Imines / chemical synthesis
Imines / chemistry
Molecular Structure
Organogold Compounds / chemistry*
Pyridones / chemical synthesis*
Pyridones / chemistry
Stereoisomerism

Substances

Alkenes
Alkynes
Amides
Imines
Organogold Compounds
Pyridones
2-hydroxypyridine