The reaction of 4-hydroxy-6H-1,3-oxazin-6-ones with amidines – a route to access new 1,3,5-triazine derivatives

The reaction of 2-aryl-5-methyl-4-hydroxy-6 H -1,3-oxazin-6-ones with 1,3-binucleophilic reagents acetamidine and benzamidine was studied. It was established that in n -propanol under reflux in the presence of sodium n -propoxide or in DMSO, the predominant reaction products were 1,3,5-triazine deri...

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Bibliographic Details
Published in:	Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 60; no. 1-2; pp. 48 - 51
Main Authors:	Levshukova, Polina O., Kolesnik, Denis A., Dosina, Margarita O., Yakovlev, Igor P., Tunguskova, Lidiya A., Kuvaeva, Elena V., Semakova, Tamara L., Ksenofontova, Galina V., Pokhodnya, Yurii G.
Format:	Journal Article
Language:	English
Published:	New York Springer US 01-02-2024 Springer Nature B.V
Subjects:	Chemistry Chemistry and Materials Science Electronic structure Organic Chemistry Pharmacy Reaction products Reagents acetamidine 1,3-oxazin-6-ones benzamidine 1,3,5-triazines 4-hydroxy-6 recyclization
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Summary:	The reaction of 2-aryl-5-methyl-4-hydroxy-6 H -1,3-oxazin-6-ones with 1,3-binucleophilic reagents acetamidine and benzamidine was studied. It was established that in n -propanol under reflux in the presence of sodium n -propoxide or in DMSO, the predominant reaction products were 1,3,5-triazine derivatives. It was shown that the reaction time and the yield of the target product were significantly influenced by the choice of the solvent, the nucleophilicity of the amidine, and the electronic structure of 4 hydroxy-6 H -1,3-oxazin-6-one.
ISSN:	0009-3122 1573-8353
DOI:	10.1007/s10593-024-03292-5