Synthesis of 3(2H)-furanone derivatives: p-TsOH/halotrimethylsilane promoted cycloketonization of γ-hydroxyl ynones

Qiu, Yi-Feng; Cao, Jian-He; Wang, Shutao; Wang, Qiang; Li, Ming; Wang, Jun-Jiao; Quan, Zheng-Jun; Wang, Xi-Cun

doi:10.1039/d3ob01500a

Cited by 6 publications

(1 citation statement)

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“…Our group has long been committed to the development of new visible-light-induced organic synthesis methods [38][39][40] ; The study of molecular properties and reaction mechanisms through computational chemistry. [41][42][43][44][45][46] Hence, we can raise a number of interesting questions: 1) How does changing the substituents of the donor and acceptor affect the strength of the interaction? 2) The electron donoracceptor interaction may be the Π-Π interaction, but we still don't know the exact distribution between them.…”

Section: Introductionmentioning

confidence: 99%

DFT study of electron donor-acceptor (EDA) complexes of 1H-indole and benzyl bromide derivatives: mechanism exploration and theoretical prediction

Liu,

Wang,

Liu

et al. 2024

Preprint

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Organic synthesis methods initiated by visible light have received increasing attention from synthetic chemists. Reactions initiated by EDA complexes do not require the use of toxic or expensive photoredox catalysts compared to traditional photoreaction processes. However, this kind of reaction requires the structure of the substrate, so it is important to study the detailed and systematic reaction mechanism for its design. The EDA complexes of substituted 1 H-indole and substituted benzyl bromide derivatives were studied by density functional theory (DFT). The difference between EDA complexes with substituents of different kinds and locations were compared by theoretical study and new EDA complex was predicted.

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Section: Introductionmentioning

confidence: 99%

DFT study of electron donor-acceptor (EDA) complexes of 1H-indole and benzyl bromide derivatives: mechanism exploration and theoretical prediction

Liu,

Wang,

Liu

et al. 2024

Preprint

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Potassium Phosphate‐Mediated Synthesis of C4‐Phosphorylated Quinolines via Cascade Cycloisomerization of Ynones

Qiu,

Li,

Wang

et al. 2024

Chemistry A European J

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A cascade phosphorylation cycloisomerization of readily accessible ynones and diphenylphosphine oxides facilitated by potassium phosphate is described, allowing for the straightforward synthesis of C4‐phosphorylated quinoline scaffolds. The formation of a C−P bond and a C−N bond is achieved in a single procedure without the need for pre‐assembled quinoline cores prior to phosphorylation. This transformation operates without the requirement for metals or oxidants and exhibits excellent compatibility with various functional groups. Furthermore, antimicrobial activity evaluation demonstrated that the synthesized C4 phosphorylated quinoline derivatives exhibited potent inhibitory activity against Staphylococcus aureus.

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Selective Synthesis of Functionalized 3(2H)‐Furanones via Tandem Michael Addition/Rearrangement/Cyclization Reaction of Aliphatic Alkynones: A Combined Experimental and Theoretical Study

Karnakova,

Kuzmin,

Ushakov

et al. 2024

Eur J Org Chem

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A novel catalyst‐ and solvent‐controlled dimerization of aliphatic alkynones through tandem Michael addition/rearrangement/cyclization sequence has been developed. The elaborated protocol provides a convenient chemo‐, regio‐ and stereoselective access to rare 3(2H)‐furanones decorated with 2‐exo‐methylene and 4‐ethenyl functionalities. A comprehensive density functional theory (DFT) study of possible reaction mechanism including ab initio molecular dynamics (AIMD) simulations and quantum theory of atoms in molecules (QTAIM) analysis of various substrate/catalyst/solvent complexes has revealed the Janus‐like behavior of the employed sodium tert‐butoxide/toluene system that is responsible both for the chemoselectivity of the initial addition step and the inhibition of the final cyclization step.

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Synthesis of 3(2H)-furanone derivatives: p-TsOH/halotrimethylsilane promoted cycloketonization of γ-hydroxyl ynones

Abstract: A p-TsOH/halotrimethylsilane facilitated cycloketonization of γ-hydroxyl ynones is detailed. This methodology enables the one-step synthesis of polysubstituted 3(2H)-furanone products. It is remarkable that the reaction exhibits excellent regio- and chemoselectivity...

Cited by 6 publications

References 50 publications

DFT study of electron donor-acceptor (EDA) complexes of 1H-indole and benzyl bromide derivatives: mechanism exploration and theoretical prediction

DFT study of electron donor-acceptor (EDA) complexes of 1H-indole and benzyl bromide derivatives: mechanism exploration and theoretical prediction

Potassium Phosphate‐Mediated Synthesis of C4‐Phosphorylated Quinolines via Cascade Cycloisomerization of Ynones

Selective Synthesis of Functionalized 3(2H)‐Furanones via Tandem Michael Addition/Rearrangement/Cyclization Reaction of Aliphatic Alkynones: A Combined Experimental and Theoretical Study

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