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Title: Synthesis and Reactivity of Electron-Deficient 3-Vinylchromones
Authors: Sosnovskikh, V. Y.
Issue Date: 2021
Publisher: Georg Thieme Verlag
Georg Thieme Verlag KG
Citation: Sosnovskikh V. Y. Synthesis and Reactivity of Electron-Deficient 3-Vinylchromones / V. Y. Sosnovskikh // SynOpen. — 2021. — Vol. 5. — Iss. 3. — P. 255-277.
Abstract: The reported methods and data for the synthesis and reactivity of electron-deficient 3-vinylchromones containing electron-withdrawing groups at the exo -cyclic double bond are summarized and systematized for the first time. The main methods for obtaining these compounds are Knoevenagel condensation, Wittig reaction, and palladium-catalyzed cross-couplings. The most important chemical properties are transformations under the action of mono- and dinucleophiles, ambiphilic cyclizations, and cycloaddition reactions. The cross-conjugated and polyelectrophilic dienone system in 3-vinylchromones provides their high reactivity and makes these compounds valuable building blocks for the preparation of more complex heterocyclic systems. Chemical transformations of 3-vinylchromones usually begin with an attack of the C-2 atom and are accompanied by the opening of the pyrone ring followed by recyclization, in which the carbonyl group of chromone, an exo -double bond or a substituent on it can take part. The mechanisms of the reactions are discussed, the conditions for their implementation are described, and the yields of the resulting products are given. This review focuses on an analysis and generalization of the knowledge that has accumulated on the chemistry of electron-deficient 3-vinylchromones, mostly over the past 15 years. 1 Introduction 2 Synthesis of 3-Vinylchromones 3 Reactions with Mononucleophiles 4 Reactions with Dinucleophiles 5 Ambiphilic Cyclization 6 Cycloaddition Reactions 7 Other Reactions 8 Conclusion. © 2021 BMJ Publishing Group. All rights reserved.
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85114702881
PURE ID: 23689988
ISSN: 2509-9396
metadata.dc.description.sponsorship: The Russian Science Foundation (project No. 18-13-00186) is acknowledged for funding.
RSCF project card: 18-13-00186
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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