Title of article :
4-Hydroxy-4-methyl-5-tosylhexahydropyrimidin-2-imines: synthesis and different dehydration pathways
Author/Authors :
Anatoly D. Shutalev، نويسنده , , Anastasia A. Fesenko، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2011
Pages :
6
From page :
6883
To page :
6888
Abstract :
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.
Keywords :
Tosyl migration , Guanidinoalkylation , 4-Tetrahydropyrimidin-2-imines , Hexahydropyrimidin-2-imines , 2 , 1 , 3
Journal title :
Tetrahedron
Serial Year :
2011
Journal title :
Tetrahedron
Record number :
1103617
Link To Document :
بازگشت