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Features of two- and multicomponent heterocyclization reactions involving 3,4-disubstituted 5-aminopyrazoles and alkyl pyruvates

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2018

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Sakhno, Yana I.
Kozyryev, Anton V.
Desenko, Sergey M.
Shishkina, Svetlana V.
Musatov, Vladimir I.
Chebanov, Valentin A.

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https://doi.org/10.1016/j.tet.2017.12.031
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Tetrahedron. 2018, 74(5), pp. 564-571. ISSN 0040-4020. eISSN 1464-5416. Available under: doi: 10.1016/j.tet.2017.12.031

Zusammenfassung

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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ISO 690SAKHNO, Yana I., Anton V. KOZYRYEV, Sergey M. DESENKO, Svetlana V. SHISHKINA, Vladimir I. MUSATOV, Dmytro SYSOIEV, Valentin A. CHEBANOV, 2018. Features of two- and multicomponent heterocyclization reactions involving 3,4-disubstituted 5-aminopyrazoles and alkyl pyruvates. In: Tetrahedron. 2018, 74(5), pp. 564-571. ISSN 0040-4020. eISSN 1464-5416. Available under: doi: 10.1016/j.tet.2017.12.031
BibTex
@article{Sakhno2018-02Featu-41405,
  year={2018},
  doi={10.1016/j.tet.2017.12.031},
  title={Features of two- and multicomponent heterocyclization reactions involving 3,4-disubstituted 5-aminopyrazoles and alkyl pyruvates},
  number={5},
  volume={74},
  issn={0040-4020},
  journal={Tetrahedron},
  pages={564--571},
  author={Sakhno, Yana I. and Kozyryev, Anton V. and Desenko, Sergey M. and Shishkina, Svetlana V. and Musatov, Vladimir I. and Sysoiev, Dmytro and Chebanov, Valentin A.}
}
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