Synthesis of <i>N-</i> and <i>C</i>-azolyl-substituted pyrazolo[1,5-<i>a</i>]pyrimidines by recyclization of pyrimidinium salts

Authors

  • Геворг Г. Данагулян Russian-Armenian (Slavonic) University, Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia
  • Аракся К. Туманян Russian-Armenian (Slavonic) University, Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia
  • Оганес С. Аттарян Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia
  • Рафаел А. Тамазян Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia
  • Анна Г. Данагулян Russian-Armenian (Slavonic) University, Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia
  • Армен Г. Айвазян Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia

DOI:

https://doi.org/10.1007/2346

Keywords:

hydrazide, pyrazole, pyrazolo[1, 5-a]pyrimidine, pyrimidinium iodide, rearrangement

Abstract

We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N-azolyl- and С-pyrazolyl-substituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-a]pyrimidine.

How to Cite
Danagulyan, G. G.; Tumanyan, A. K.; Attaryan, O. S.; Tamazyan, R. A.; Danagulyan, A. G.; Ayvazyan, A. G. Chem. Heterocycl. Compd. 2015, 51, 483. [Khim. Geterotsikl. Soedin. 2015, 51, 483.]

For this article in the English edition see DOI 10.1007/s10593-015-1724-3

 

Author Biographies

Геворг Г. Данагулян, Russian-Armenian (Slavonic) University, Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia

Геворг Грачевич Данагулян

зав. лабораторией ИОХ НАН РА,

проф. РАУ, чл-корр. НАН РА

Аракся К. Туманян, Russian-Armenian (Slavonic) University, Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia

Аракся Карушевна Туманян

канд.  хим.  наук

Оганес С. Аттарян, Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia

Оганес Саркисович Аттарян

канд.  хим.  наук

Рафаел А. Тамазян, Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia

Рафаел Аршамович Тамазян

к. ф-м. н.

Анна Г. Данагулян, Russian-Armenian (Slavonic) University, Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia

Анна Геворговна Данагулян

м. н. с

Армен Г. Айвазян, Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia

Армен Григорьевич Айвазян

м. н. с

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Published

2015-05-22

Issue

Vol. 51 No. 5 (2015)

Section

Original Papers