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Chemical transformations of 3-amino-2-quinolones

✍ Scribed by Silvia E. Asías; Ana M. Bruno; Diego A. Dominici; Mariela Bollini; Carlos H. Gaozza

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
80 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

In order to find new antimalarial drugs, an exploration about the chemical properties of the starting compounds 3‐amino‐6‐chloro‐4‐phenyl‐1__H__‐quinolin‐2‐one (1) and 3‐amino‐4‐methyl‐1__H__‐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.

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