Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 5, Pages 818-822Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901257
Keywords
Nitrogen heterocycles; Annulation; Friedlander reaction; Dimerization; Ketones
Categories
Funding
- National Science Foundation of China [20942001]
- Guangzhou Institute of Biomedicine and Health (GIBH)
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Reactions between readily available 2-alkynylanilines and activated ketones such as beta-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2,3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquinolines, which are difficult to obtain by classical methods such as the Friedlander reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C-4.
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