Chemical transformations of 3‐amino‐2‐quinolones

Abstract

AbstractIn order to find new antimalarial drugs, an exploration about the chemical properties of the starting compounds 3‐amino‐6‐chloro‐4‐phenyl‐1H‐quinolin‐2‐one (1) and 3‐amino‐4‐methyl‐1H‐quinolin‐2‐one (2) was developed. Acylation with acyl chloride, sulfonyl chloride and acetic anhydride were carried out. Despite a previous report [2], when acetyl chloride or acetic anhydride were assayed on 1, only the diacetyl derivative 7 was obtained. When this compound was heated at reflux temperature in a mixture of acetic acid and acetic anhydride, it was transformed in the oxazoloquinoline 8. Further reactions of the acyl derivatives with diazomethane afforded 1‐methylated compounds. Compound 2 gave the imine 16 by condensation with 4‐nitrobenzaldehyde.