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CC BY 4.0 · SynOpen 2023; 07(02): 258-266
DOI: 10.1055/a-2091-7934
paper

Temperature-Controlled Diastereoselective Doebner/Ugi Tandem Reaction

Yana Sakhno∗
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
,
Oleksandr Radchenko
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
b   Faculty of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine
,
Vyacheslav Saraev
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
,
Yuliia Shliapkina
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
,
Mariia Kaidash
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
,
Mariia Shyshkina
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
,
Svitlana Shishkina
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
b   Faculty of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine
,
Vladimir Musatov
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
,
Sergey Desenko
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
,
Valentyn Chebanov  ∗
a   Division of Chemistry of Functional Materials, State Scientific Institution ‘Institute for Single Crystals’ NAS of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine
b   Faculty of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine
› Author AffiliationsThe project of National Research Foundation of Ukraine ‘Polypharmacophoric organic compounds based on peptidomimetics and fused benzodiazepines’ (2020.02/0023), and the Royal Society of Chemistry (grant R22-1038807649).
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Abstract

Novel peptidomimetics containing a pyrrolone fragment were synthesized by a tandem combination of Doebner and Ugi type multicomponent reactions with controlled diastereoselectivity. This approach represents a convenient synthesis in the temperature range from 25 to 45 °C. In most cases, the new method allowed each diastereomer to be isolated separately.

Keywords

multicomponent reactions - Doebner reaction - Ugi reaction - peptidomimetics - pyrrolones - diastereoselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2091-7934.
  • Supporting Information


Publication History

Received: 19 April 2023

Accepted after revision: 10 May 2023

Accepted Manuscript online:
11 May 2023

Article published online:
31 May 2023

© 2023. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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