Investigation of the Sulfide Contraction Sequence for Synthesizing 2-Amino-4-Quinolones

Abstract

Quinalones have over the years gained attention as a class of antibacterial agents (Albrecht, 1977). A tremendous amount of synthetic research is aimed at improving the performance of these compounds. The C02H group at the 3 position is considered essential, as well as a fluorine atom at the 7 position, although many modifications on the skeleton have been explored (Schentag and Domagala, 1985). Few studies involving substitution at the 2 position have been conducted (Schentag and Domagala, 1985). One recent study (Chu et al., 1985) concluded that substitution of a sulfur atom at the 2 position could lead to useful compounds. The purpose of this project is to investigate the use of the sulfide contraction sequence in preparing starting materials for the synthesis of quinalones, in particular those with amino substituents at the C2 position.