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

Геворг Г. Данагулян, Аракся К. Туманян, Оганес С. Аттарян, Рафаел А. Тамазян, Анна Г. Данагулян, Армен Г. Айвазян
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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

 


Keywords


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

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