Pd/C–Cu mediated direct and one-pot synthesis of γ-ylidene butenolides

Rambabu, D.; Bhavani, S.; Nalivela, Kumara Swamy; Mukherjee, Somenath; Rao, Mandava V. Basaveswara; Pal, Manojit

doi:10.1016/j.tetlet.2013.02.040

Cited by 18 publications

(20 citation statements)

References 42 publications

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“…To the best of our knowledge, only a handful of examples of heterogeneous protocols for the cycloisomerization of alkynoic acids to the corresponding lactones exist to this date. 24,25,29 We have recently reported on the preparation of a heterogeneous catalyst based on Pd nanoparticles immobilized on amino-functionalized siliceous mesocellular foam (Pd(0)-AmP-MCF). 30,31 Mesocellular foam (MCF) is a mesoporous material that has proven to be an excellent support for both chemical as well as biological catalysts, mainly due to its high surface area, high pore volume and adjustable pore size.…”

Section: Introductionmentioning

confidence: 99%

Cycloisomerization of Acetylenic Acids to γ-Alkylidene Lactones using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam

et al. 2014

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Cycloisomerization of various γ-acetylenic acids to their corresponding γ-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well as internal alkynes were cyclized in high to excellent yields within 2-24 h under mild reaction conditions. The procotol exhibited high regio-and stereoselectivity, favoring the exo-dig product with high (Z)-selectivity. Moreover, the catalyst displayed excellent stability under the employed reaction conditions, as demonstrated by its good recyclability and low leaching.

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Section: Introductionmentioning

confidence: 99%

Cycloisomerization of Acetylenic Acids to γ-Alkylidene Lactones using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam

et al. 2014

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“…General analysis of the oxidation process of 5-(hydroxymethyl) furfural (1). Compounds: 5-(hydroxymethyl)furfural (1), 5-methylenefuran-2(5H)-one (protoanemonin) (2), maleic acid (4), acetic acid (5), maleic anhydride (11), malonic acid (6), succinic acid (8), malic acid (9), and glycolic acid (10). acid could be transferred from the aqueous phase of hydrogen peroxide to the organic phase of chlorinated solvent, improving the interaction with the substrates in the same phase.…”

Section: Self-catalysed Oxidation Process: Generation Of Formic Acid mentioning

confidence: 99%

“…Plausible mechanism for the formation of protoanemonin (2) and diverse organic acids through a complex oxidation process. Compounds: 5-Methylenefuran-2(5H)-one (2), (Z)-5-hydroxy-4-oxopent-2-enoic acid (3), maleic acid (4), acetic acid (5), malonic acid (6), 5-(hydroxymethyl)furan-2-ol (7), succinic acid (8), malic acid (9), and glycolic acid (10) were identified by 1 H NMR analysis of the reaction crude mixture (See Figures 2 and 3). Table 2.…”

Section: Self-catalysed Oxidation Process: Generation Of Formic Acid mentioning

confidence: 99%

“…Monitoring of the oxidation reaction of 5-(hydroxymethyl)furfural (1) by 1 H NMR analysis. [a] Time (h) [b] 70 30 6 5 5 --4 ----4 [b] 100 60 -7 9 --11 ----8 [b] 100 22 -14 6 4 12 16 ----24 [c] 100 --1 -22 -1 30 21 7 13 [a] Reaction conditions: 5-(hydroxymethyl)furfural 1 2, 5-(hydroxymethyl)furan-2-ol (7), formic acid (FA), (Z)-5-hydroxy-4-oxopent-2-enoic acid (3), maleic acid (4), maleic anhydride (11), acetic acid (5), malonic acid (6), succinic acid (8), malic acid (9), and glycolic acid (10).…”

Section: Self-catalysed Oxidation Process: Generation Of Formic Acid mentioning

confidence: 99%

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Obtaining Protoanemonin through Selective Oxidation of D‐Fructose and 5‐(Hydroxymethyl)furfural in a Self‐catalysed Reaction

et al. 2020

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Although different ways of converting 5-(hydroxymethyl)furfural (1) to various substrates with high value have been sought, few transformations have obtained building blocks that can be very useful in the area of fine chemistry. Herein, we report the synthesis of protoanemonin (5-methylenefuran-2(5H)-one) from D-fructose via compound (1), a versatile γ-alkylidenebutenolide, using an efficient selfcatalysed process with formic acid, with high reaction performance and selectivity (up to 94% yield and 98% conversion from (1), while 28% yield from D-fructose). This efficient and simple operational process involved a two-phase aqueous-organic system between chlorinated solvents (CH x Cl y) and hydrogen peroxide as the initial oxidizing agent. The reaction presents a key cleavage in the 5-hydroxymethyl moiety of (1), due to the Baeyer-Villiger oxidation (BVO) process that generates formic acid in situ. Ultimately, DFF and HMF were successfully obtained in 80% and 98% yield, respectively, starting from D-fructose and using Preyssler heteropolyacids as Brønsted acid catalysts under an atmosphere of oxygen in the absence of hydrogen peroxide.

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“…Furthermore, the synthesis of the protoanemonin from 2-deoxy-Dribose also has been reported [18]. One-pot synthesis of protoanemonin was achieved by a catalyst system composed by the combination of 10% Pd/C with CuI, PPh 3 , and Et 3 N coupling of (Z)-3-iodoacrylic acid and trimethylsilyl acetylene [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxic evaluation of protoanemonin and three brominated derivatives

Pañeda¹,

Apan²

2020

Rev. Colomb. Quim.

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The protoanemonin, a natural furanone, was synthesized from (Z)-4-bromo-5-(bromomethylene)-furan-2(5H)-one by a reductive dehalogenation reaction with zinc. The 5-(dibromomethylene)-2(5H)-furanone and (E)-5-(bromomethylene)-2(5H)-furanone were also synthetized from levulinic acid bromination and acid promoted cyclization. The antiproliferative activity of all synthesized compounds against the human cancer cell lines PC-3 (prostate) and U-251 (glioblastoma) was investigated. The results showed that all the obtained furanones are more active than the reference drug cisplatin, with IC50 values in the range of 0.31 ± 0.02 to 7.30 ± 0.08 μM. However, (E)-5-(bromomethylene)-2(5H)-furanone, with a bromine atom in the double bond, was the most active, and demonstrated to be about 25-fold more active than the reference drug cisplatin.

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Pd/C–Cu mediated direct and one-pot synthesis of γ-ylidene butenolides

Cited by 18 publications

References 42 publications

Cycloisomerization of Acetylenic Acids to γ-Alkylidene Lactones using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam

Cycloisomerization of Acetylenic Acids to γ-Alkylidene Lactones using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam

Obtaining Protoanemonin through Selective Oxidation of D‐Fructose and 5‐(Hydroxymethyl)furfural in a Self‐catalysed Reaction

Synthesis and cytotoxic evaluation of protoanemonin and three brominated derivatives

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