Synthesis of β,γ-unsaturated primary amides from α,β-unsaturated acids and investigation of the mechanism

Théodorou, Vassiliki; Gogou, Marina; Philippidou, Maria; Ragoussis, Valentine; Paraskevopoulos, Georgios; Skobridis, Konstantinos

doi:10.1016/j.tet.2011.05.096

Cited by 9 publications

(3 citation statements)

References 44 publications

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“…The amides 11-13 had been prepared by reaction of the sec-amine (2 mmol) in dry THF (10 mL) with the appropriate acid chloride, CH 3 COCl or PhCOCl, (1 mmol) in dry THF or dry CH 2 Cl 2 at 0 °C under argon 26 . After addition was complete, the mixture was stirred for a further 1-2 h at room temperature, then refluxed for about 1 h until completion.…”

Section: Methodsmentioning

confidence: 99%

A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

Théodorou¹,

Paraskevopoulos²,

Skobridis³

2015

Arkivoc

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A mild protocol for the alkaline hydrolysis of secondary and tertiary amides in non-aqueous conditions, by the use of NaOH in methanol/dichloromethane or methanol/dioxane (1:9) at room temperature or under reflux, has been developed and a plausible reaction mechanism is discussed. Primary amides are hydrolyzed much slower than with the classical procedure, while nitriles are converted selectively to primary amides.

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Section: Methodsmentioning

confidence: 99%

A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

Théodorou¹,

Paraskevopoulos²,

Skobridis³

2015

Arkivoc

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“…The close proximity of the double bonds might also favor a double bond shift into conjugation during biosynthesis with concomitant double bond isomerization, leading to 2 E ,4 E -C12:2-HSL. Furthermore, deconjugation is a known process known to occur during formation of α,β-unsaturated amides under basic conditions, leading potentially to 3 E ,5 Z -C12:2-HSL [23,24]. Therefore, we decided to synthesize all three compounds to reveal insight into the MS and GC behavior of the isomers and also allowing to perform bioassays to investigate whether slight changes in double bond location and geometry have an influence on the activity in AHL reporter assays.…”

Section: Resultsmentioning

confidence: 99%

“…Finally, acid 10 was coupled with HSL·HBr in the presence of EDC·HCl and p -dimethylaminopyridine (DMAP) to furnish N -((2 E ,5 Z )-2,5-dodecadienoyl)homoserine lactone ( 11 ). The isomerization of the double bond, leading again to 13 , can also be induced by the use of triethylamine in this step instead of the weaker base DMAP [24]. AHL 11 is not stable for prolonged storage under room temperature, leading to the isomerized compound 13 and other stereoisomers.…”

Section: Resultsmentioning

confidence: 99%

An Unprecedented Medium-Chain Diunsaturated N-acylhomoserine Lactone from Marine Roseobacter Group Bacteria

et al. 2018

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N-acylhomoserine lactones (AHLs), bacterial signaling compounds involved in quorum-sensing, are a structurally diverse group of compounds. We describe here the identification, synthesis, occurrence and biological activity of a new AHL, N-((2E,5Z)-2,5-dodecadienoyl)homoserine lactone (11) and its isomer N-((3E,5Z)-3,5-dodecadienoyl)homoserine lactone (13), occurring in several Roseobacter group bacteria (Rhodobacteraceae). The analysis of 26 strains revealed the presence of 11 and 13 in six of them originating from the surface of the macroalgae Fucus spiralis or sediments from the North Sea. In addition, 18 other AHLs were detected in 12 strains. Compound identification was performed by GC/MS. Mass spectral analysis revealed a diunsaturated C12 homoserine lactone as structural element of the new AHL. Synthesis of three likely candidate compounds, 11, 13 and N-((2E,4E)-2,4-dodecadienoyl)homoserine lactone (5), revealed the former to be the natural AHLs. Bioactivity test with quorum-sensing reporter strains showed high activity of all three compounds. Therefore, the configuration and stereochemistry of the double bonds in the acyl chain seemed to be unimportant for the activity, although the chains have largely different shapes, solely the chain length determining activity. In combination with previous results with other Roseobacter group bacteria, we could show that there is wide variance between AHL composition within the strains. Furthermore, no association of certain AHLs with different habitats like macroalgal surfaces or sediment could be detected.

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Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives

Bedford

2014

Organic Reaction Mechanisms Series

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Synthesis of β,γ-unsaturated primary amides from α,β-unsaturated acids and investigation of the mechanism

Cited by 9 publications

References 44 publications

A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

An Unprecedented Medium-Chain Diunsaturated N-acylhomoserine Lactone from Marine Roseobacter Group Bacteria

Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives

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