Triacetic acid lactone as a bioprivileged molecule in organic synthesis

Обыденнов, Дмитрий Л.; El-Tantawy, Asmaa I.; Sosnovskikh, Vyacheslav Ya.

doi:10.1016/j.mencom.2019.01.001

Cited by 30 publications

(21 citation statements)

References 127 publications

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“…In addition to exploring alternatives for the midblock in ABA copolymers, we also sought to replace styrene with renewable feedstocks for use in synthesizing the glassy component in TPEs. We chose 4-hydroxy-6-methyl-2-pyrone [denoted as triacetic acid lactone (TAL)], which can be obtained synthetically from acetic acid − or through biological pathways in select microbes, which synthesize the compound as a secondary metabolite of glucose and other sugars. − Notably, ongoing research into the genetic bioengineering of Escherichia coli and Saccharomyces cerevisiae suggests that biologically synthesized TAL may be a viable feedstock. − Although TAL and its numerous derivatives have been studied for their efficacy as food preservatives, antimicrobials, pharmaceuticals, and so forth, its use as a renewable feedstock for polymer synthesis has yet to be explored in detail. ,, In a recent study, partial substitution of p(epichlorohydrin) with TAL via postpolymerization modification resulted in an apparent increase in the T g of the material from −30 °C up to 70 °C depending on the degree of substitution …”

Section: Introductionmentioning

confidence: 99%

Block Copolymer Pressure-Sensitive Adhesives Derived from Fatty Acids and Triacetic Acid Lactone

Sajjad

Tolman

Reineke

2020

ACS Appl. Polym. Mater.

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A method for the development of ABA triblock copolymers for high-performance pressure-sensitive adhesives from the biorenewable chemicals lauryl acrylate and triacetic acid lactone (TAL) is presented. Lauryl acrylate, readily derived from vegetable oils, was polymerized via a reversible addition− fragmentation chain-transfer process to yield high-molecularweight telechelic polymers. The synthesis of triblock copolymers was accomplished by subsequent chain extension with TAL, which is available from carbohydrates via the action of genetically modified yeast. The resulting triblock copolymers were found to exhibit excellent adhesion, with tunable peel forces up to 8 N cm −1 when a rosin ester-based tackifier was used. Tack forces up to 7 N cm −1 and no shear failure up to 100 h demonstrate the competitive performance of the potentially sustainable adhesives with commercial commodity products.

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Section: Introductionmentioning

confidence: 99%

Block Copolymer Pressure-Sensitive Adhesives Derived from Fatty Acids and Triacetic Acid Lactone

Sajjad

Tolman

Reineke

2020

ACS Appl. Polym. Mater.

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“…Lauryl acrylate is readily derived from vegetable oils, including coconut and palm kernel oils, , and was investigated as an alternative to n- butyl acrylate as a rubbery midblock in ABA triblock copolymers. To replace frequently styrenic glassy end blocks, the authors investigated derivatives of 4-hydroxy-6-methyl-2-pyrone ( 2 - 75 ), which is produced as a secondary metabolite of glucose and other sugars by some microbes − or may be synthesized from acetic acid. − Catalytic hydrogenation of the pyrone proceeded over a period of 2 to 3 days; the authors attribute the extended reaction time to slow internal keto–enol tautomerization following partial reduction (Scheme ). Nonetheless, the transformation afforded the corresponding lactone ( 2 - 76 ) in near-quantitative yields.…”

Section: Feedstocksmentioning

confidence: 99%

Defining the Macromolecules of Tomorrow through Synergistic Sustainable Polymer Research

et al. 2022

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Transforming how plastics are made, unmade, and remade through innovative research and diverse partnerships that together foster environmental stewardship is critically important to a sustainable future. Designing, preparing, and implementing polymers derived from renewable resources for a wide range of advanced applications that promote future economic development, energy efficiency, and environmental sustainability are all central to these efforts. In this Chemical Reviews contribution, we take a comprehensive, integrated approach to summarize important and impactful contributions to this broad research arena. The Review highlights signature accomplishments across a broad research portfolio and is organized into four wide-ranging research themes that address the topic in a comprehensive manner: Feedstocks, Polymerization Processes and Techniques, Intended Use, and End of Use. We emphasize those successes that benefitted from collaborative engagements across disciplinary lines.

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“…Particular attention is paid to 4-hydroxy-2-pyrones, namely, triacetic acid lactone (TAL), dehydroacetic acid (DHA, Figure 1 ), and their derivatives, which belong to polyketides and occur widely in living organisms [ 5 , 6 , 7 , 8 ]. The availability of these compounds and the possibility of their biochemical synthesis contributed to their extensive research and to the development of a wide range of options for their modification, considering them as platform compounds [ 9 , 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones

et al. 2022

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Dehydroacetic acid and triacetic acid lactone are known to be versatile substrates for the synthesis of a variety of azaheterocycles. However, their fluorinated analogs were poorly described in the literature. In the present work, we have investigated reactions of trifluorotriacetic acid lactone and hexafluorodehydroacetic acid with primary amines, phenylenediamine, and phenylhydrazine. While hexafluorodehydroacetic acid reacted the same way as non-fluorinated analog giving 2,6-bis(trifluoromethyl)-4-pyridones, trifluorotriacetic acid lactone had different regioselectivity of nucleophilic attack compared to the parent structure, and corresponding 3-amino-6,6,6-trifluoro-5-oxohex-3-eneamides were formed as the products. In the case of binucleophiles, further cyclization took place, forming corresponding benzodiazepine and pyrazoles. The obtained 2,6-bis(trifluoromethyl)-4-pyridones were able to react with active methylene compounds giving fluorinated merocyanine dyes.

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Triacetic acid lactone as a bioprivileged molecule in organic synthesis

Cited by 30 publications

References 127 publications

Block Copolymer Pressure-Sensitive Adhesives Derived from Fatty Acids and Triacetic Acid Lactone

Block Copolymer Pressure-Sensitive Adhesives Derived from Fatty Acids and Triacetic Acid Lactone

Defining the Macromolecules of Tomorrow through Synergistic Sustainable Polymer Research

Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones

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