Features of two- and multicomponent heterocyclization reactions involving 3,4-disubstituted 5-aminopyrazoles and alkyl pyruvates |
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| Authors: | Yana I Sakhno Anton V Kozyryev Sergey M Desenko Svetlana V Shishkina Vladimir I Musatov Dmytro O Sysoiev Valentin A Chebanov |
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| Institution: | 1. Division of Chemistry of Functional Materials, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky Ave. 60, 61072, 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 |
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| Abstract: | Three-component heterocyclizations of pyruvic acids and their esters with 5-aminopyrazoles and aromatic aldehydes, in addition to the sequential versions of these reactions, under different activating conditions were studied. Under conventional heating, pyrazolopyrimidine derivatives containing a hydroxyl group in the 6-position were formed in both two- and three-component treatments. Whereas the application of an inert atmosphere did not influence the outcome of these reactions, the use of ultrasonic irradiation led to the formation of 7-hydroxy-tetrahydropyrazolopyrimidines in multi-component reactions and 6-hydroxy-dihydropyrazolopyrimidines in the case of a step-by-step approach. The products of the latter treatment were further transformed into heteroaromatized 6-hydroxy-pyrazolopyrimidines by conventional heating. |
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| Keywords: | Aminoazole Alkyl pyruvates Ultrasonication Multicomponent reaction |
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