4-Hydroxy-4-methyl-5-tosylhexahydropyrimidin-2-imines: synthesis and different dehydration pathways

Synthesis of 4-hydroxy-4-methyl-5-tosylhexahydropyrimidin-2-imines by reaction of N-cyano- N′-(1-tosylalk-1-yl)guanidines with enolates of tosylacetone was developed. Base-catalyzed dehydration of the obtained pyrimidines gave the expected 6-methyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-imines. Howev...

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Bibliographic Details
Published in:Tetrahedron 2011-09, Vol.67 (36), p.6883-6888
Main Authors: Shutalev, Anatoly D., Fesenko, Anastasia A.
Format: Article
Language:English
Subjects:
1,2,3,4-Tetrahydropyrimidin-2-imines
Dehydration
Derivatives
Guanidinoalkylation
Hexahydropyrimidin-2-imines
Migration
Pathways
Pyrimidines
Solvents
Synthesis (chemistry)
Tetrahedrons
Tosyl migration
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Summary:Synthesis of 4-hydroxy-4-methyl-5-tosylhexahydropyrimidin-2-imines by reaction of N-cyano- N′-(1-tosylalk-1-yl)guanidines with enolates of tosylacetone was developed. Base-catalyzed dehydration of the obtained pyrimidines gave the expected 6-methyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-imines. However, their acid-catalyzed dehydration led to mixtures of the latter compounds and the products of tosyl group migration, 4-tosylmethyl derivatives. This reaction was strongly influenced by the nature of the solvent. Plausible explanations of the obtained data were given. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.06.088