Concise Two-Step Synthesis of γ-Pyrone from Acetone

Hobuß, Dennis; Baro, Angelika

doi:10.1055/s-2004-835620

Cited by 10 publications

(2 citation statements)

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“…The two-step sequence was described in the literature on a gram scale. 7 However, the first step suffered from several drawbacks such as the use of a large excess of BF 3 • OEt 2 and the need for cryogenic conditions. We successfully reproduced the procedures, but all our efforts to reduce the amount of Lewis acid and to perform the reaction under noncryogenic conditions failed (see Figure S1 in the Supporting Information).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Our initial strategy hinged upon the construction of γ-pyrone 9 starting from diacetal 10 made from acetone and triethyl orthoformate. The two-step sequence was described in the literature on a gram scale . However, the first step suffered from several drawbacks such as the use of a large excess of BF 3 ·OEt 2 and the need for cryogenic conditions.…”

Section: Introductionmentioning

confidence: 99%

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Tetrahydro-4H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

Zahim¹,

Delacroix²,

Carlier³

et al. 2021

Org. Process Res. Dev.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tetrahydro-4H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

Zahim¹,

Delacroix²,

Carlier³

et al. 2021

Org. Process Res. Dev.

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Fluorinated Pyrones, Chromones and Coumarins

Sosnovskikh

2014

Fluorine in Heterocyclic Chemistry Volume 2

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Synthesis and In Situ Behavior of 1,4- and 2,5-(¹³C) Isotopomers of p-Phenylenediamine in Reconstructed Human Epidermis Using High Resolution Magic Angle Spinning NMR

Srour

Gosset

Moussallieh

et al. 2022

Chem. Res. Toxicol.

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Para-phenylenediamine (PPD) has been classified as a strong skin allergen but when it comes to toxicological concerns, benzoquinone diamine (BQDI), the primary oxidation derivative of PPD, is frequently considered and was shown to covalently bind nucleophilic residues on model peptides. However, tests in solution are far from providing a reliable model as the cutaneous metabolism of PPD is not covered. We now report the synthesis of two 13 C substituted isotopomers of PPD, 1,4-( 13 C)p-phenylenediamine 1 and 2,5-( 13 C)pphenylenediamine 2, and the investigation of their reactivity in reconstructed human epidermis (RHE) using high resolution magic angle spinning (HRMAS) NMR technique. RHE samples were first treated with 1 or 2 and incubated for 1 to 48 h. Compared to the control, spectra clearly showed only the signals of 1 or 2 gradually decreasing with time to disappear after 48 h of incubation. However, the culture media of RHE incubated with 1 for 1 h and 24 h, respectively, showed the presence of both monoacetylated-and diacetylated-PPD as major products.Therefore, the acetylation reaction catalyzed by N-acetyltransferase (NAT) enzymes appeared to be the main process taking place in RHE. With the aim of increasing the reactivity by oxidation, 1 and 2 were treated with 0.5 equiv. H2O2 prior to their application to RHE and incubated for different times. Under these conditions, new peaks having close chemical shifts to those of PPDcysteine adducts previously observed in solution were detected. Under such oxidative conditions, we were thus able to detect and quantify cysteine adducts in RHE (maximum of 0.2 nmol/mg of RHE at 8 h of incubation) while no reaction with other nucleophilic amino acid residues could be observed.

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Concise Two-Step Synthesis of γ-Pyrone from Acetone

Abstract: g-Pyrone (1) is readily accessible in 59% overall yield via 1,1,5,5-tetraethoxy-3-pentanone (10b) and subsequent acidic hydrolysis. The synthesis enables an easy scale up, as demonstrated for intermediate 10b.

Cited by 10 publications

References 3 publications

Tetrahydro-4H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

Tetrahydro-4H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

Fluorinated Pyrones, Chromones and Coumarins

Synthesis and In Situ Behavior of 1,4- and 2,5-(¹³C) Isotopomers of p-Phenylenediamine in Reconstructed Human Epidermis Using High Resolution Magic Angle Spinning NMR

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Concise Two-Step Synthesis of γ-Pyrone from Acetone

Abstract: g-Pyrone (1) is readily accessible in 59% overall yield via 1,1,5,5-tetraethoxy-3-pentanone (10b) and subsequent acidic hydrolysis. The synthesis enables an easy scale up, as demonstrated for intermediate 10b.

Cited by 10 publications

References 3 publications

Tetrahydro-4H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

Tetrahydro-4H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

Fluorinated Pyrones, Chromones and Coumarins

Synthesis and In Situ Behavior of 1,4- and 2,5-(13C) Isotopomers of p-Phenylenediamine in Reconstructed Human Epidermis Using High Resolution Magic Angle Spinning NMR

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About

Synthesis and In Situ Behavior of 1,4- and 2,5-(¹³C) Isotopomers of p-Phenylenediamine in Reconstructed Human Epidermis Using High Resolution Magic Angle Spinning NMR