New Heterocyclisation Reactions of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Some 1,3-Dielectrophilic Agents

5-Amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile enters into condensation reactions with β-diketones and dibenzalacetone to form 2-(cyanomethyl)pyrazolo[1,5- a ]pyrimidine-3-carbonitrile derivatives. The reaction with cyanoguanidine in an acid medium leads to the formation of 2,4-diamino-7-(cyan...

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Bibliographic Details
Published in:Russian journal of general chemistry 2022-03, Vol.92 (3), p.367-382
Main Authors: Semenova, A. M., Gadzhiakhmedova, Ya. R., Bespalov, A. V., Dotsenko, V. V., Aksenov, N. A., Aksenova, I. V.
Format: Article
Language:English
Subjects:
Bioavailability
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Condensates
Diketones
Proteins
Pyrazole
Pyrimidines
Quantum chemistry
Zaleplon
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Summary:5-Amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile enters into condensation reactions with β-diketones and dibenzalacetone to form 2-(cyanomethyl)pyrazolo[1,5- a ]pyrimidine-3-carbonitrile derivatives. The reaction with cyanoguanidine in an acid medium leads to the formation of 2,4-diamino-7-(cyanomethyl)pyrazolo[1,5- a ][1,3,5]triazine-8-carbonitrile. Structure of the obtained compounds was confirmed by spectral data, as well as the results of a quantum chemical study of possible reaction routes for the reaction of 5-amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile with benzoyltrifluoroacetone. Bioavailability parameters were predicted for the obtained products in silico , and possible protein targets were predicted by protein-ligand docking.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363222030057