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Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates

Authors :
Joachim Horn
Gordon G. Weingarten
Adam Nelson
Stephen P. Marsden
David House
Source :
Organic letters. 10(18)
Publication Year :
2008

Abstract

A direct convergent two-component synthesis of quinolines from alpha,beta-unsaturated ketones and o-aminophenylboronic acid derivatives is reported. The reaction is regiocomplementary to the traditional Skraup-Doebner-Von Miller synthesis and proceeds under basic rather than strongly acidic conditions. Quinolines substituted in the benzenoid ring can be accessed by using substituted o-aminophenylboronates prepared by direct palladium-catalyzed borylation of the corresponding o-bromoanilines.

Details

ISSN :
15237052
Volume :
10
Issue :
18
Database :
OpenAIRE
Journal :
Organic letters
Accession number :
edsair.doi.dedup.....7b01b9fb478b3dba860e1d13e02596e6