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New Access to 2,3-Disubstituted Quinolines through Cyclization of o-Alkynylisocyanobenzenes

Michinori Suginome, Takeshi Fukuda and Yoshihiko Ito*

*Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan

M. Suginome, T. Fukuda, Y. Ito, Org. Lett., 1999, 1, 1977-1979.

DOI: 10.1021/ol991133w (free Supporting Information)


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Abstract

A nucleophile-induced intramolecular cyclization of o-alkynylisocyanobenzenes provides 2,3-disubstituted quinoline derivatives in high yields. In addition to oxygen and nitrogen nucleophiles such as methanol and diethylamine, the nucleophilic carbon of the enolate of malonate induced the cyclization effectively.

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Key Words

quinolines


ID: J54-Y1999