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

We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N -azolyl- and С -pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and f...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2015-05, Vol.51 (5), p.483-490
Main Authors: Danagulyan, Gevorg G., Tumanyan, Araksya K., Attaryan, Oganes S., Tamazyan, Rafael A., Danagulyan, Anna G., Ayvazyan, Armen G.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Esters
Organic acids
Organic Chemistry
Pharmacy
Pyrimidines
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Summary:We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N -azolyl- and С -pyrazolylsubstituted 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-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5- a ]pyrimidine.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-015-1724-3