A direct and vicinal functionalization of the 1-methyl-2-quinolone framework: 4-alkoxylation and 3-chlorination?

Organic & Biomolecular Chemistry Pub Date: 2016-05-06 DOI: 10.1039/C6OB00868B

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.

Graphical abstract: A direct and vicinal functionalization of the 1-methyl-2-quinolone framework: 4-alkoxylation and 3-chlorination
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