Synthesis and Reactivity of Electron-Deficient 3-Vinylchromones
Vyacheslav Ya. Sosnovskikh
- Vol. 05, Iss: 03, pp 255-277
TLDR
The literature data on the methods of 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 in this paper.Abstract:
The literature data on the methods of 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 at it can take part. The mechanisms of the reactions are discussed, the conditions for their implementation and the yields of the resulting products are indicated. 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.read more
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References
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Journal ArticleDOI
Domino inverse electron demand Diels-Alder reactions of chromones with ethyl vinyl ether
Ramiro Araya-Maturana,Jorge Heredia-Moya,Karsten Krohn,Ulrich Flörke,Hernán Pessoa-Mahana,Boris E. Weiss-López,Ana Estévez-Braun +6 more
TL;DR: Inverse electron demand Diels-Alder (IEDDA)-elimination-IEDDA generates isomeric tetracycles as discussed by the authors, yielding 2-hydroxybenzophenones.
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TL;DR: Le produit d'aldolisation du compose du titre reagit avec des silyl enol ethers pour conduire a des oxo-2' alkyl-2 t-butyldimethylsiloxy-4 chromeneacrylates-3 d'ethyle as mentioned in this paper.
Journal ArticleDOI
Unusual Acid- and Base-Catalyzed C–N Bond Formation Approach through Reaction of Chromonyl Meldrum’s Acid and Nitrogen Binucleophiles
TL;DR: In this paper, the reaction of chromonyl Meldrum's acid and N-substituted 2-aminobenzamides was studied in the presence of acidic and basic catalysts.
Journal ArticleDOI
Cascade reactions between 2-substituted-3-(4-oxo-4H-chromen-3-yl)acrylonitriles with benzylamine and p-toluidine
TL;DR: In this paper, simple condensation products derived from 3-formylchromone and some active methylene compounds, were achieved by reaction with nucleophilic reagents namely benzylamine and p-toluidine to produce either 2-iminopyrane or pyrano[3,2-c]chromene derivatives.
Journal ArticleDOI
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