SYNTHESIS OF N-ALKYLATED DERIVATIVES OF PYRAZOLO[1,5-<i>a</i>]PYRIMIDINE AND THEIR REACTION WITH METHYLAMINE

Authors

  • Г. Г. Данагулян Institute of Organic Chemistry, National Academy of Sciences, Yerevan 375094
  • Г. А. Паносян Center of Molecular Structure Investigation, National Academy of Sciences, Yerevan 375014
  • А. П. Бояхчян Institute of Organic Chemistry, National Academy of Sciences, Yerevan 375094

Keywords:

iodoalkylates, methylamine, pyrazolo[1,5-a]pyrimidine, destruction, NOEDIF method, rearrangement, NMR

Abstract

With the object of studying the factors influencing the course of enamine rearrangements, we have carried out the N-alkylation of alkyl- and aryl-substituted pyrazolo[1,5-a]pyrimidines. Using the NOEDIF NMR spectroscopic method for the cases of 5,7-dimethyl-2-phenyl- and 2,5,7-triphenylpyrazolo[1,5-a]pyrimidines it was found that addition of the alkyl group occurs at the N(4) atom of the pyrimidine fragment in the pyrazolo[1,5-a]pyrimidine. It was shown that, when reacting with an alcoholic solution of methylamine, the 5,7-dimethyl-2-phenyl- and 2,5,7-triphenylpyrazolo[1,5-a]pyrimidine iodomethylates undergo decomposition to give 5-methylamino-3-phenylpyrazole and 5-(1,3-diphenyl-3-methylamino-2-propenylid-1-ene)amino-3-phenylpyrazole.

How to Cite
Danagulyan, G. G.; Panosyan, G. A.; Boyakhchyan, A. P. Chem. Heterocycl. Compd. 2002, 38, 581. [Khim. Geterotsikl. Soedin. 2002, 665.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1019517414682

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Published

2002-05-25

Issue

No. 5 (2002)

Section

Original Papers