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Multicomponent reactions of ethyl trifluoroacetoacetate with carbonyl and nucleophilic reagents as a promising tool for organic synthesis

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Abstract

The review is summarized and systematized the published data on the multicomponent reactions of ethyl trifluoroacetoacetate, carbonyl compounds (aldehydes and ketones), and nucleophilic reagents. The recent advances in the study of the Hantzsch and Biginelli reactions involving polyfluoroalkyl-3-oxo esters are analyzed. These transformations tolerated a broad range of the nucleophilic reagents thus allowing the synthesis of a wide variety of hetero- and carbocyclic compounds including the derivatives of pyridine, pyrimidine, pyrazole, pyran, dioxane, and isoxazole as well as their heterofused derivatives. The reactivity characteristics of ethyl trifluoroacetoacetate with different reagents in these multicomponent transformations are discussed.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoy, 620108, Ekaterinburg, Russian Federation

    S. O. Kushch, M. V. Goryaeva, Ya. V. Burgart & V. I. Saloutin

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  1. S. O. Kushch
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  2. M. V. Goryaeva
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  3. Ya. V. Burgart
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  4. V. I. Saloutin
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Correspondence to V. I. Saloutin.

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This work was financially supported by the Russian Science Foundation (Project No. 21-13-00390).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Saloutin Viktor Ivanovich, born in 1952, Corresponding Member of the Russian Academy of Sciences, Chief Researcher of the I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences (IOS UB RAS), Head of the Laboratory of organofluorine compounds and the Direction of programs and platforms of the same Institute, Candidate for Full Member of the Russian Academy of Sciences in the elections of 2022. V. I. Saloutin is the specialist in organofluorine chemistry, he is the author of 416 articles, five monographs, and 48 inventor’s certificates and patents. His main scientific interests include the design of fluorine-containing compounds based on multicarbonyl compounds promising for the synthesis of biologically active substances and advanced materials. V. I. Saloutin developed simple and elegant approach to the synthesis of fluorinated heteroanalogs of marine ascidian alkaloids by autocatalyzed three-component cyclization of fluorinated 3-keto esters, methyl carbonyl compounds, and amines; developed an integrated approach to the selective synthesis of fluorinated analogs of antipyrine and efficient synthetic methods towards trifluoromethyl-4-nitroso- and -4-aminopyrazoles showing the pronounced antibacterial activity. He elaborated the methods for transformation and analysis of polychlorinated biphenyls as pretreatment for their microbiological utilization. With participation of V. I. Saloutin, the fluorine-containing materials and working fluids for the special-purpose technologies were developed and introduced into the pilot production. V. I. Saloutin is actively engaged in pedagogical activity. He supervised 17 doctoral students and 2 habilitations. V. I. Saloutin was awarded the Order of Friendship (2002) and honorary title “Merited Scientist of the Russian Federation” (2008). V. I. Saloutin is a recipient of the International Academic Publishing Company “Nauka/Interperiodika” award for the best publication in journals of the Russian Academy of Sciences (2008). He was awarded the I. Ya. Postovsky prize of the UB RAS (2010) and the Diploma Di Merito of the European Scientific-Industrial Chamber of the European Union. V. I. Saloutin is a member of the Bureau of the Division of Chemistry and Materials Science of RAS, a member of the Scientific Council of RAS on organic and organoelement chemistry, a member of the Joint Scientific Council on Chemical Sciences of UB RAS, a member of the Scientific Council of IOS UB RAS, a member of Central Scientific Library of UB RAS, a member of the Council for awarding the degree of Doctor of Chemical Sciences (Habilitation) at the Ural Federal University, and a member of the International Society of Heterocyclic Chemistry.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 1, pp. 103–129, January, 2023.

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Kushch, S.O., Goryaeva, M.V., Burgart, Y.V. et al. Multicomponent reactions of ethyl trifluoroacetoacetate with carbonyl and nucleophilic reagents as a promising tool for organic synthesis. Russ Chem Bull 72, 103–129 (2023). https://doi.org/10.1007/s11172-023-3717-1

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