- Triacetic acid lactone as a common intermediate for the synthesis of 4-hydroxy-2-pyridones and 4-amino-2-pyrones
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At ambient temperature, triacetic acid lactone reacts with amines to produce 4-amino-2-pyrones. If the temperature is raised to 100 °C, 4-hydroxy-2-pyridones are generated.
- Kraus, George A.,Wanninayake, Umayangani K.,Bottoms, Jashaun
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p. 1293 - 1295
(2016/03/01)
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- Reactivite de la methyl-6 hydroxy-4 pyrone-2 vis-a-vis des amines primaires : synthese de pyridones-2 N-substituees et d'hexanamides intermediaires
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In the well-documented (1-7) reaction of ammonia or primary amines with 2-pyrones leading to pyridones, the aliphatic intermediates have never been isolated, except for the reaction of 1 with aniline (8).In this work, the reaction of 4-hydroxy-6-methyl-2-pyrone 1 with various primary amines is studied.Three 5-amino-3-oxo-4-hexaneamides 3 are isolated for the first time and characterized by NMR, IR and mass spectra.The corresponding 4-hydroxy-6-methyl-2-pyridones 4 are obtained by heating intermediates 3.Direct attack of 1 by primary amines yields the same compounds 4 and finally leads to 4-alkyl (or phenyl) amino-6-methyl-2-pyridones 5.Thus, compounds of the type 5 are obtained from 4-hydroxy-6-methyl-2-pyrone 1 in for steps including three successive nucleophilic sustitutions by primary amines.
- Castillo, Simone,Ouadahi, Hamid,Herault, Valentin
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p. 257 - 261
(2007/10/02)
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