SYNTHESIS AND OXIDATIVE AROMATIZATION OF 5-ACETYL-2-CYANOIMINO-6-METHYL-4-PHENYL-1,2,3,4-TETRAHYDROPYRIMIDINE WITH MANGANESE DIOXIDE

被引：8
|
作者：
Solovyev, P. A. [1 ]
Shutalev, A. D. [1 ]
机构：
[1] MV Lomonosov Moscow State Acad Fine Chem Technol, Moscow 119571, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2009年 / 45卷 / 07期
关键词：
2-aminopyrimidines; manganese dioxide; 2-imino-1,2-dihydropyrimidines; 2-imino-1,2,3,4-tetrahydropyrimidines; guanidinoalkylation; oxidative aromatization; SYMMETRICAL HETEROARYL CARBOXAMIDES; ORGANIC-CHEMISTRY; CCR5; ANTAGONISTS; HIV-1; TAUTOMERISM; DERIVATIVES; ALKALOIDS;
D O I：
10.1007/s10593-009-0357-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of 5-acetyl-2-cyanoimino-6-methyl-4-phenyl-1,2,3,4-tetrahydropyrimidine has been carried out by reaction of N-[(tosyl)(phenyl) methyl]-N'-cyanoguanidine with acetylacetone in the presence of sodium hydride with subsequent acid catalyzed dehydration of the 4-hydroxy-2-imino-hexahydropyrimidine obtained. The oxidative aromatization of the tetrahydropyrimidine synthesized using manganese dioxide has been studied. It was found that the products formed depend on the reaction temperature and are either 5-acetyl-2-carbamoylamino-4-methyl-6-phenylpyrimidine or 5-acetyl-2-amino-4-methyl-6-phenylpyrimidine or a mixture of both.
引用
收藏
页码：809 / 814
页数：6
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