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Reactions of 4‐pyrones with primary amines. A new class of ionic associates
Author(s) -
Van Allan J. A.,
Reynolds G. A.,
Alessi J. T.,
Chang S. Chie,
Joines R. C.
Publication year - 1971
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.5570080606
Subject(s) - chemistry , primary (astronomy) , ionic bonding , perchloric acid , derivative (finance) , titration , alkyl , medicinal chemistry , organic chemistry , salt (chemistry) , ion , physics , astronomy , financial economics , economics
Primary aliphatic amines react with 2,6‐dimethyl‐4‐pyrone to give 2,6‐dialkylamino‐2,5‐heptadien‐4‐one derivatives. When the alkyl group was methyl, the diamino derivative cyclized on warming to give 1,2,6‐trimethyl‐4‐pyridone. The corresponding butylamino derivative did not thermally cyclize, but did give a pyridone on treatment with acid. The isopropylaminoketone did not cyclize. Several examples of 1,2,6‐trisubstituted‐4‐pyridones formed “ionic associates” consisting of two parts of the pyridone and one part of perchloric acid. These associates are useful primary standards for nonaqueous titrations.