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Updated: Mar 21, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
A direct and vicinal functionalization of the 1-methyl-2-quinolone framework: 4-alkoxylation and 3-chlorination
Feiyue Hao1, Haruyasu Asahara, Nagatoshi Nishiwaki
1School of Environmental Science and Engineering, Kochi University of Technology, Miyanokuchi, Tosayamada, Kami, Kochi 782-8502, Japan. nishiwaki.nagatoshi@kochi-tech.ac.jp.
Abstract:
Bis(functionalization), 4-alkoxylation and 3-chlorination, of the 1-methyl-2-quinolone framework was achieved under mild conditions by a sequential treatment of 3-nitrated 1-methyl-2-quinolones with sodium alkoxide and N-chlorosuccinimide. Moreover, a succinimide group instead of an alkoxy group was introduced at the 4-position, affording a masked form of the 4-amino-3-chloro-2-quinolone derivative. Furthermore, the prepared vicinally functionalized quinolones thus obtained were subjected to a Suzuki-Miyaura coupling reaction, arylating the 3-position.
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