☆ 4.8 Article

Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates

ORGANIC LETTERS (2008)

期刊

ORGANIC LETTERS

卷 10, 期 18, 页码 4117-4120

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol8016726

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Chemistry, Organic

资金

EPSRC
Glaxo-SmithKline [EP/E020712/1]
EPSRC [EP/E020712/1] Funding Source: UKRI
Engineering and Physical Sciences Research Council [EP/E020712/1, GR/S99419/01] Funding Source: researchfish

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摘要

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.

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