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Synthesis 2011(11): 1723-1732  
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

Lijie Peng, Honggen Wang, Changlan Peng, Ke Ding*, Qiang Zhu*
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. of China
Fax: +86(20)32015299; e-Mail: ding_ke@gibh.ac.cn; e-Mail: zhu_qiang@gibh.ac.cn;
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Publication History

Received 1 March 2011
Publication Date:
15 April 2011 (online)

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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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