Base-Promoted Reactions in Ionic Liquid Solvent: Synthesis of Butenolides

Villemin, Didier; Mostefa‐Kara, Bachir; Bar, Nathalie; Choukchou‐Braham, Noureddine; Cheikh, Nawel; Benmeddah, Amel; Hazimeh, Hassan; Ziani-Cherif, Chewki

doi:10.2174/157017806778341807

Cited by 15 publications

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“…84 The synthesis of this kind of compound involves a base-catalyzed transesterification, followed by a Knoevenagel reaction favored by the Thorpe-Ingold effect. 85 Villemin et al 86 investigated the synthesis of butenolides 17 using ionic liquids with ethyl cyanoacetate 16, and several R-hydroxyketones 15 (Scheme 5). Different ionic liquids were tested before retaining [BMIM][BF 4 ] for its easy preparation and convenience.…”

Section: Furansmentioning

confidence: 99%

Ionic Liquids in Heterocyclic Synthesis

et al. 2008

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Section: Furansmentioning

confidence: 99%

Ionic Liquids in Heterocyclic Synthesis

et al. 2008

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“…The synthesis of this kind of compound involves a base-catalyzed transesterification, followed by a Knoevenagel reaction favored by the Thorpe–Ingold effect . Villemin et al investigated the synthesis of butenolides 17 using ionic liquids with ethyl cyanoacetate 16 , and several α-hydroxyketones 15 (Scheme ). Different ionic liquids were tested before retaining [BMIM][BF 4 ] for its easy preparation and convenience.…”

Section: Synthesis Of Five-membered Heterocyclesmentioning

confidence: 99%

Update 1 of: Ionic Liquids in Heterocyclic Synthesis

et al. 2014

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“…The 13DC reaction of NOs with substituted 2(5H)furanones (25HFs) leads to regioisomeric 2-isoxalines which are important intermediates for the synthesis of interesting heterocyclic systems [1,2]. We note that 25HF derivatives are present in a wide range of biologically active natural [3] and synthetic [4][5][6][7][8][9] products and can act as excellent dipolarophiles in 13DC reactions or as dienophiles in Diels-Alder reactions [10][11][12][13]. According to experimental results, the regioselectivity of 13DC reactions of NOs are affected by the electronic effects of the substituents present in the dipole and the dipolarophile partners [1,14,15].…”

Section: Introductionmentioning

confidence: 99%

Prediction of the Regioselectivity of 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides with 2(5H)-Furanones Using Recent Theoretical Reactivity Indices

Charif

Benchouk

Mekelleche

2017

Progress in Reaction Kinetics and Mechanism

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The regioselectivity of a series of 16 1,3-dipolar cycloaddition reactions of nitrile oxides with 2(5 H)-furanones has been analysed by means of global and local electrophilic and nucleophilic reactivity indices using density functional theory at the B3LYP level together with the 6-31G(d) basis set. The local electrophilicity and nucleophilicity indices, based on Fukui and Parr functions, have been calculated for the terminal sites, namely the C1 and O3 atoms of the 1,3-dipole and the C4 and C5 atoms of the dipolarophile. These local indices were calculated using both Mulliken and natural charges and spin densities. The results obtained show that the C5 atom of the 2(5 H)-furanones is the most electrophilic site whereas the O3 atom of the nitrile oxides is the most nucleophilic centre. It turns out that the experimental regioselectivity is correctly reproduced, indicating that both Fukui- and Parr-based indices are efficient tools for the prediction of the regiochemistry of the studied reactions and could be used for the prediction of new designed reactions of the same kind.

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Base-Promoted Reactions in Ionic Liquid Solvent: Synthesis of Butenolides

Cited by 15 publications

References 0 publications

Ionic Liquids in Heterocyclic Synthesis

Ionic Liquids in Heterocyclic Synthesis

Update 1 of: Ionic Liquids in Heterocyclic Synthesis

Prediction of the Regioselectivity of 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides with 2(5H)-Furanones Using Recent Theoretical Reactivity Indices

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