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

被引：8
|
作者：
Shutalev, Anatoly D. [1 ]
Fesenko, Anastasia A. [1 ]
机构：
[1] Moscow State Acad Fine Chem Technol, Dept Organ Chem, Moscow 119571, Russia
来源：
TETRAHEDRON | 2011年 / 67卷 / 36期
关键词：
Hexahydropyrimidin-2-imines; 1,2,3,4-Tetrahydropyrimidin-2-imines; Guanidinoalkylation; Tosyl migration; NATURAL GUANIDINE DERIVATIVES; ALLYLIC SULFONES;
D O I：
10.1016/j.tet.2011.06.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6883 / 6888
页数：6
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