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Synthesis 2011(11): 1723-1732
DOI: 10.1055/s-0030-1260001
DOI: 10.1055/s-0030-1260001
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Sequential Hydration-Condensation-Double Cyclization of Pyridine-Substituted 2-Alkynylanilines: An Efficient Approach to Quinoline-Based Heterocycles
Further Information
Received
1 March 2011
Publication Date:
15 April 2011 (online)
Publication History
Publication Date:
15 April 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201111/lookinside/thumbnails/10.1055-s-0030-1260001-1.jpg)
Abstract
An environmentally benign and atom-economical process to construct a unique quinoline-based tetracyclic scaffold, through sequential hydration-condensation-double cyclization reactions, has been described. The reaction starts with readily available pyridine-substituted o-alkynylanilines and β-keto esters, promoted by p-toluenesulfonic acid in ethanol in one pot. In the absence of β-keto esters, multisubstituted quinolines are formed bimolecularly in reasonable yields.
Key words
alkynes - cyclization - heterocycles - quinoline - tandem reaction
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