Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products |
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| Authors: | Maryna V. Murlykina Yana I. Sakhno Sergey M. Desenko Iryna S. Konovalova Oleg V. Shishkin Dmytro A. Sysoiev Maryna N. Kornet Valentin A. Chebanov |
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| Affiliation: | 1. Division of Chemistry of Functional Materials, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Lenin Ave. 60, 61001 Kharkiv, Ukraine;2. Faculty of Chemistry, V.N. Karazin Kharkiv National University, Svobody Sq. 4, 61077 Kharkiv, Ukraine;3. Fachbereich Chemie, University of Konstanz, Fach M-720, Universitaetsstrasse 10, 78457 Konstanz, Germany;4. Laboratory of Biotechnology of Physiologically Active Substances, Zaporizhzhya National University, Zhukovsky Str. 66, Zaporizhzhya 69600, Ukraine |
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| Abstract: | Three-component reactions of 5-aminopyrazoles and salicylic aldehydes with pyruvic acids were studied. The method of tuning of the selectivity of the heterocyclizations allowing to change its direction by variation of the reaction parameters was worked out. The treatment involving pyruvic acid can be selectively directed to the formation to either 3-aryl-10,11-dihydro-4,10-methano-pyrazolo[4,3-c][1,5]benzoxazocine-4-carboxylic acids or 3,6-diarylpyrazolo[3,4-b]pyridine-4-carboxylic acids, while the reaction involving arylpyruvic acid leads only to 7-hydroxy-2,5,6-triaryl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine-7-carboxylic acids. Antimicrobial activity of the compounds obtained was also studied: Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) were found sensitive to the substances tested, however, only in the highest concentration. |
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| Keywords: | Aminoazole Salicylaldehyde Pyruvic acids Ultrasound Multicomponent reaction |
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