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

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journal contribution
posted on 12.11.1999, 00:00 by Michinori Suginome, Takeshi Fukuda, Yoshihiko Ito
o-Alkynylisocyanobenzenes underwent nucleophile-induced intramolecular cyclization to give 2,3-disubstituted quinoline derivatives in high yields. In addition to the oxygen and nitrogen nucleophiles such as methanol and diethylamine, the nucleophilic carbon of the enolate of malonate induced the cyclization effectively. Reaction of 1,4-di(trimethylsilylethynyl)-2,3-diisocyanobenzene with methanol afforded 2,9-dimethoxy-1,10-phenanthroline in good yield.