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

Authors

  • П. А. Соловьев M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Moscow 119571
  • А. Д. Шуталев M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Moscow 119571

DOI:

https://doi.org/10.1007/6640

Keywords:

2-aminopyrimidines, manganese dioxide, 2-imino-1, 2-dihydropyrimidines, 2, 3, 4-tetrahydropyrimidines, guanidinoalkylation, oxidative aromatization

Abstract

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.

How to Cite
Solovyev, P. A.; Shutalev, A. D.  Chem. Heterocycl. Compd. 2009, 45, 809. [Khim. Geterotsikl. Soedin. 2009, 1023.]

For this article in the English edition see DOI 10.1007/s10593-009-0357-9

 

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Published

2022-03-01

Issue

No. 7 (2009)

Section

Original Papers