Chemistry of Substituted Quinolinones. Part VI. Synthesis and Nucleophilic Reactions of 4-Chloro-8-methylquinolin-2(1H)-one and its Thione Analogue

Abstract

The synthesis of 4-chloro-8-methylquinolin-2(1H)-one and its thione analogue is described. Some nucleophilic substitution reactions of the 4-chloro group were carried out to get new 4-substituted 2-quinolinones and quinolinethiones, such as 4-sulfanyl, hydrazino, azido and amino derivatives, which are of important synthetic use. The structure of the new compounds was established by their elemental analysis, IR and 1H-NMR spectra. Also the mass fragmentation pattern of some products is discussed.

Keywords

• quinolinone
• quinolinethione
• nucleophilic substitution
• thiol-thione tautomerism
• mass fragmentation