Practical and simple synthesis of substituted quinolines by an HCl-DMSO system on a large scale: remarkable effect of the chloride ion

Shin-Ya Tanaka; Makoto Yasuda; Akio Baba

doi:10.1021/jo052004y

Practical and simple synthesis of substituted quinolines by an HCl-DMSO system on a large scale: remarkable effect of the chloride ion

J Org Chem. 2006 Jan 20;71(2):800-3. doi: 10.1021/jo052004y.

Authors

Shin-Ya Tanaka¹, Makoto Yasuda, Akio Baba

Affiliation

¹ Department of Applied Chemistry and Handai Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 16408997
DOI: 10.1021/jo052004y

Abstract

[reaction: see text] A variety of substituted quinolines are synthesized from imines and enolizable carbonyl compounds under aerobic conditions, in which only water is a byproduct. In DMSO, a catalytic amount of HCl activates carbonyl compounds quite effectively to give the quinolines. A simple and practical procedure is demonstrated on a large scale.

Publication types

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

MeSH terms

Chlorides
Dimethyl Sulfoxide
Hydrochloric Acid
Indicators and Reagents
Models, Molecular
Molecular Conformation
Quinolines / chemical synthesis*
Quinolines / chemistry*

Substances

Chlorides
Indicators and Reagents
Quinolines
Hydrochloric Acid
Dimethyl Sulfoxide