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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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2013

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Murlykina, Maryna V.
Sakhno, Yana I.
Desenko, Sergey M.
Konovalova, Iryna S.
Shishkin, Oleg V.
Kornet, Maryna N.
Chebanov, Valentin A.

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https://doi.org/10.1016/j.tet.2013.08.055
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Tetrahedron. 2013, 69(44), pp. 9261-9269. ISSN 0040-4020. eISSN 1464-5416. Available under: doi: 10.1016/j.tet.2013.08.055

Zusammenfassung

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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540 Chemie

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ISO 690MURLYKINA, Maryna V., Yana I. SAKHNO, Sergey M. DESENKO, Iryna S. KONOVALOVA, Oleg V. SHISHKIN, Dmytro SYSOIEV, Maryna N. KORNET, Valentin A. CHEBANOV, 2013. Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products. In: Tetrahedron. 2013, 69(44), pp. 9261-9269. ISSN 0040-4020. eISSN 1464-5416. Available under: doi: 10.1016/j.tet.2013.08.055
BibTex
@article{Murlykina2013-11Featu-42262,
  year={2013},
  doi={10.1016/j.tet.2013.08.055},
  title={Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products},
  number={44},
  volume={69},
  issn={0040-4020},
  journal={Tetrahedron},
  pages={9261--9269},
  author={Murlykina, Maryna V. and Sakhno, Yana I. and Desenko, Sergey M. and Konovalova, Iryna S. and Shishkin, Oleg V. and Sysoiev, Dmytro and Kornet, Maryna N. and Chebanov, Valentin A.}
}
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