Ionic Liquid as Catalyst and Reaction Medium: A Simple and Efficient Procedure for Paal–Knorr Furan Synthesis

Wang, Gangqiang; Guan, Zhi; Tang, Rongchang; He, Yan‐Hong

doi:10.1080/00397910902978049

Cited by 24 publications

(5 citation statements)

References 26 publications

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“…1 H NMR (CDCl 3 ) δ 8.53 (m, 1H), 8.08 (m, 1H), 8.00 (m, 1H), 7.76 (t, 1H), 7.55 (t, 1H), 7.43 (t, 2H), 7.31 (m, 2H), 6.78 (d, J = 3.5 Hz, 1H), 6.89 (d, J = 3.5 Hz, 1H); 13 C NMR (CDCl 3 ) δ 154.7, 150.7, 148.8, 132.2, 130.1, 129.7, 129.0, 128.8, 128.0, 124.0, 121.5, 119.2, 109.5, 107.4. The 1 H and 13 C NMR data are in accord with literature data …”

Section: Methodssupporting

confidence: 85%

Formation of Allenyl Ketones, 3-Ethynylcoumarins, and Arylfurans, Furylfurans, and Furylthiophenes by Flash Vacuum Thermolysis of 3-Methylidenefuran-2(3H)-ones

2013

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Flash vacuum thermolysis (FVT) of 3-methylidenefuran-2(3H)-ones 3 causes cheletropic extrusion of CO with formation of allenyl ketones 4. o-Chloro- and o-bromophenylmethylidenefuranones also afford allenyl ketones upon flash vacuum thermolysis, but in addition, 3-ethynylcoumarins 6 are formed via E/Z isomerization of the methylidenefuranones, cyclization, halogen atom migration, and HCl (HBr) elimination. The presence of strongly electron-withdrawing groups (nitroaryl or acetyl) on the acylallene moiety causes rearrangement to give 2-arylfurans 10 and 13 as well as 2-furylfurans and 2-furylthiophenes 16 by cyclization of the allenyl ketones. The reaction mechanisms are supported by calculations at the M06-2X/6-311+G(d,p) level of theory.

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Section: Methodssupporting

confidence: 85%

Formation of Allenyl Ketones, 3-Ethynylcoumarins, and Arylfurans, Furylfurans, and Furylthiophenes by Flash Vacuum Thermolysis of 3-Methylidenefuran-2(3H)-ones

2013

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“…[21b] The formation of small amounts of MTHFA and HD attributes to the fact that hydrogenation of furan ring of MFA and hydration of DMF took place during the reaction. [22][23][24] The yields of MTHFA and HD were, however, below 3 % even after 20 h, which suggests that these side reactions occur at much slower rates. Mechanistically, we postulate that the zinc component facilitates hydrogenolysis of BHMF to DMF by cleavage of CÀO bonds, as discussed in our earlier report involving HDO of phenolic alcohols and aldehydes.…”

Section: The Effect Of Reaction Timementioning

confidence: 99%

Zinc‐Assisted Hydrodeoxygenation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Dimethylfuran

2014

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2,5-Dimethylfuran (DMF), a promising cellulosic biofuel candidate from biomass derived intermediates, has received significant attention because of its low oxygen content, high energy density, and high octane value. A bimetallic catalyst combination containing a Lewis-acidic Zn(II) and Pd/C components is effective for 5-hydroxymethylfurfural (HMF) hydrodeoxygenation (HDO) to DMF with high conversion (99%) and selectivity (85% DMF). Control experiments for evaluating the roles of zinc and palladium revealed that ZnCl2 alone did not catalyze the reaction, whereas Pd/C produced 60% less DMF than the combination of both metals. The presence of Lewis acidic component (Zn) was also found to be beneficial for HMF HDO with Ru/C catalyst, but the synergistic effect between the two metal components is more pronounced for the Pd/Zn system than the Ru/Zn. A comparative analysis of the Pd/Zn/C catalyst to previously reported catalytic systems show that the Pd/Zn system containing at least four times less precious metal than the reported catalysts gives comparable or better DMF yields. The catalyst shows excellent recyclability up to 4 cycles, followed by a deactivation, which could be due to coke formation on the catalyst surface. The effectiveness of this combined bimetallic catalyst has also been tested for one-pot conversion of fructose to DMF.

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“…2,5-Hexanedione was probably formed via the reverse of the Paal-Knorr synthesis. 30,31 The Paal-Knorr synthesis is a reaction to synthesize furans or pyrroles from 1,4diketones, which is catalyzed by acids. 30,31 2,5-Hexanedione is a 1,4-diketones and opening of the furan ring via the reverse Paal-Knorr synthesis was a possible route for its formation.…”

Section: Conversion Of Hmf In Watermentioning

confidence: 99%

Simultaneous hydrogenation and acid-catalyzed conversion of the biomass-derived furans in solvents with distinct polarities

Kadarwati

Song

et al. 2016

RSC Adv.

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Ionic Liquid as Catalyst and Reaction Medium: A Simple and Efficient Procedure for Paal–Knorr Furan Synthesis

Cited by 24 publications

References 26 publications

Formation of Allenyl Ketones, 3-Ethynylcoumarins, and Arylfurans, Furylfurans, and Furylthiophenes by Flash Vacuum Thermolysis of 3-Methylidenefuran-2(3H)-ones

Formation of Allenyl Ketones, 3-Ethynylcoumarins, and Arylfurans, Furylfurans, and Furylthiophenes by Flash Vacuum Thermolysis of 3-Methylidenefuran-2(3H)-ones

Zinc‐Assisted Hydrodeoxygenation of Biomass‐Derived 5‐Hydroxymethylfurfural to 2,5‐Dimethylfuran

Simultaneous hydrogenation and acid-catalyzed conversion of the biomass-derived furans in solvents with distinct polarities

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