15250-44-9Relevant academic research and scientific papers
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
Castillo, Simone,Ouadahi, Hamid,Herault, Valentin
, p. 257 - 261 (2007/10/02)
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.
