4-Pyridone Explained

4-Pyridone is an organic compound with the formula . It is a colorless solid.

Preparation

4-Pyridone, and its derivatives, are prepared from 4-pyrone and amines in protic solvents.^{[1] [2] [3]}

Tautomerism

4-Pyridone exists a keto-enol tautomerism with its enol tautomer 4-hydroxypyridine. In solution, the keto tautomer is favoured, and the enol tautomer only becomes important in very dilute solutions or solutions of non-polar solvents. However, the enol tautomer is dominant in the gas phase.^[4]

Derivatives

Fluridone is an aquatic herbicide that contains a 4-pyridone subunit.^[5]

See also

• 2-Pyridone
• 4-Piperidone
• Dehydroacetic acid

Notes and References

1. Book: Weygand. Conrad. Hilgetag. G.. Martini. A.. Weygand/Hilgetag Preparative Organic Chemistry. 1972. John Wiley & Sons, Inc.. New York. 0471937495. 533–534. 4th.
2. Van Allan. J. A.. Reynolds. G. A.. Alessi. J. T.. Chie Chang. S.. C. Joines. R.. Reactions of 4-pyrones with primary amines. A new class of ionic associates. Journal of Heterocyclic Chemistry. 1971. 8. 6. 919–922. 10.1002/jhet.5570080606.
3. Cook. Denys. The Preparation, Properties, and Structure of 2,6-bis-(Alkyamino)-2,5-heptadien-4-ones. Canadian Journal of Chemistry. 1963. 41. 6. 1435–1440. 10.1139/v63-195.
4. Book: Joule . John A. . Mills . Keith . Heterocyclic Chemistry . Wiley-Blackwell . Oxford . 2000-06-29 . 0-632-05453-0. 88-91.
5. Book: 10.1002/14356007.o28_o01 . Weed Control, 2. Individual Herbicides . Ullmann's Encyclopedia of Industrial Chemistry . 2011 . Müller . Franz . Applebyki . Arnold P. . 978-3-527-30385-4 .