Unexpected behaviour of tosylated and acetylated imidazolinium salts

Clemens, Nicole; Sereda, Oksana; Wilhelm, René

doi:10.1039/b601104g

Cited by 8 publications

(7 citation statements)

References 24 publications

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“…The synthesis of compound 4 has been previously reported . The title compound was isolated in small amounts via a decarboxylation of imidazoline 1 .…”

Section: Methodsmentioning

confidence: 99%

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Nuclear Factor-κB Mediated Inhibition of Cytokine Production by Imidazoline Scaffolds

et al. 2009

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The mammalian nuclear transcription factor NF-kappaB is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-alpha) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-kappaB has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-kappaB mediated gene transcription in cell culture as well as inhibitors of TNF-alpha and IL-6 production in interleukin 1 beta (IL-1beta) stimulated human blood.

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“…The synthesis of compound 4 has been previously reported . The title compound was isolated in small amounts via a decarboxylation of imidazoline 1 .…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of compound 4 has been previously reported. 44 The title compound was isolated in small amounts via a decarboxylation of imidazoline 1. A solution of imidazoline 1 (0.7 g, 1.62 mmol) in 100 mL of THF was refluxed for 5 h, resulting in complete decomposition of starting material.…”

Section: Dl-(4r5rmentioning

confidence: 99%

Nuclear Factor-κB Mediated Inhibition of Cytokine Production by Imidazoline Scaffolds

et al. 2009

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“…In dioxane under reflux a low yield of 6% was obtained with a low endo / exo ratio of (3:1). Salt 8 [25] and 9 [25] gave similar poor results as salt 7 [25]. Finally, the bis-imidazolinium salt 10 [12] gave the product in 69% yield with an endo / exo ratio comparable to BF 3 •Et 2 O.…”

Section: Resultsmentioning

confidence: 94%

“…Next, imidazolinium salt 7 [25] was used in the reaction. The formation of the product was observed at 45 °C; however, the product was isolated only in a low yield of 8%.…”

Section: Resultsmentioning

confidence: 99%

Imidazolinium and amidinium salts as Lewis acid organocatalysts

Sereda¹,

Clemens²,

Heckel³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThe application of imidazolinium and amidinium salts as soft Lewis acid organocatalysts is described. These salts were suitable catalysts for the activation of unsaturated thioesters in a Diels–Alder reaction and in the ring opening of thiiranes and epoxides. The products were isolated in good yields. The mild catalysts did not cause desulfurization of the products containing a thiol or thiocarbonyl group.

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“…By using the ethylene ketal of 2-bromopropiophenone as a test substrate, it was demonstrated that the active sites in [Cu 3 (btc) 2 ] are hard Lewis acids. 46 Several tetrasubstituted cyclopentanes (51) can be prepared in four steps from cyclopentadiene in good overall yield (30%) by the acid-catalysed rearrangement of epoxide (49) followed by a regio-and stereo-selective nucleophilic attack, with control of the relative configuration of four contigous stereogenic centres in a single operation (Scheme 14). 39 The fragmentations of 3-nortricyclyl, exo-5-norbornen-2-yl, and endo-5-norbornen-2-yl oxychlorocarbenes, chlorocarbonates, and chlorosulfites in polar solvents proceed via similar ion pairs to mixtures of exo-2-chloro-5-norbornene and 3-nortricyclyl chloride.…”

Section: Cationic Rearrangementsmentioning

confidence: 99%

Molecular Rearrangements: Part 2. Other Reactions

Brandi

Gensini

2010

Organic Reaction Mechanisms · 2006

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The formation of α-phenyl-β-halovinyl cation, β-phenyl-α-halovinyl cation, and also the halogen-bridged and the spirocyclic phenyl-bridged cations, as intermediates of protonation of phenylethynyl halides, or of halogen addition to phenylethynes, has been evaluated by DFT at the B3LYP/6-31+G(d) level and, for comparison in representative cases, by B3LYP/6-311++G(d,p). 1 Structural and mechanistic studies of the lithium diisopropylamide (LDA)-mediated anionic Fries rearrangements of aryl carbamates have been described. 2 Substituents at the meta position of the arene (H, OMe, F) and the dialkylamino moiety of the carbamate (Me 2 N, Et 2 N, and i-Pr 2 N) markedly influence the relative rates of ortholithiation and subsequent Fries rearrangement. The mechanism of the Fries rearrangement of aryl formates promoted by boron trichloride has been studied by means of 1 H, 2 H, and 11 B NMR spectroscopy and DFT calculations. 3 After the formation of a 1:1 substrate -Lewis acid adduct, the rearrangement proceeds in two steps, beginning with the cleavage of the ester bond and the release of formyl chloride in situ, which, in turn, acts as a formylating agent, introducing 451

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Unexpected behaviour of tosylated and acetylated imidazolinium salts

Abstract: Tosylated and acetylated imidazolinium salts revealed an unexpected reactivity when treated with methyl iodide or benzyl bromide. Moreover an unprecedented acid-catalysed rearrangement for an acetylated imidazolinium salt was observed during an anion metathesis.

Cited by 8 publications

References 24 publications

Nuclear Factor-κB Mediated Inhibition of Cytokine Production by Imidazoline Scaffolds

Nuclear Factor-κB Mediated Inhibition of Cytokine Production by Imidazoline Scaffolds

Imidazolinium and amidinium salts as Lewis acid organocatalysts

Molecular Rearrangements: Part 2. Other Reactions

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