Synthesis and Reactivity of Electron-Deficient 3-Vinylchromones
Vyacheslav Ya. Sosnovskikh
- Vol. 05, Iss: 03, pp 255-277
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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
More filters
Journal ArticleDOI
Reaction of N-Monosubstituted Hydrazones with Nitroolefins: A Novel Regioselective Pyrazole Synthesis
Xiaohu Deng,Neelakandha S. Mani +1 more
TL;DR: A novel regioselective synthesis of substituted pyrazoles from N-monosubstituted hydrazones and nitroolefins using a key nitropyrazolidine intermediate is characterized and a plausible mechanism is proposed.
Journal ArticleDOI
Palladium(II)-Catalyzed Direct Intermolecular Alkenylation of Chromones
Donghee Kim,Sungwoo Hong +1 more
TL;DR: A new efficient method for the direct alkenylation of chromones via a palladium(II)-catalyzed C-H functionalization reaction was developed and afforded various 3-vinylchromone derivatives, which are privileged structures in many biologically active compounds and versatile synthetic building blocks.
Journal ArticleDOI
Synthesis and reactions of halogen-containing chromones
TL;DR: In this paper, published data on the synthesis and reactivity of halogen-containing chromones, flavones, thiochromones and furochromones are generalised.
Journal ArticleDOI
An Enantioselective Inverse‐Electron‐Demand Imino Diels–Alder Reaction
Vincent Eschenbrenner-Lux,Vincent Eschenbrenner-Lux,Philipp Küchler,Philipp Küchler,Slava Ziegler,Kamal Kumar,Kamal Kumar,Herbert Waldmann,Herbert Waldmann +8 more
TL;DR: The first enantioselective IEDIDA reaction between electron-poor chromone dienes and cyclic imines, catalyzed by zinc/binol complexes is described, providing a facile entry to a natural product inspired collection of ring-fused quinolizines including a potent modulator of mitosis.
Journal ArticleDOI
The synthesis of pyridine derivatives from 3‐formylchromone
TL;DR: In this article, the pyridine ring forming reactions are discussed and the factors determining the formation and regiospecificity of the ring-forming reactions are also discussed, as well as the properties of pyridines.
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