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Chemical transformations of 3‐amino‐2‐quinolones
Author(s) -
Asías Silvia E.,
Bruno Ana M.,
Dominici Diego A.,
Bollini Mariela,
Gaozza Carlos H.
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400114
Subject(s) - chemistry , acetic anhydride , acylation , acetyl chloride , benzoyl chloride , diazomethane , acetic acid , organic chemistry , oxalyl chloride , derivative (finance) , chloride , chloroacetyl chloride , imine , pummerer rearrangement , medicinal chemistry , catalysis , financial economics , economics
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.