Superelectrophilic Chemistry of Imidazoles

Sheets, Matthew; Li, Ang; Bower, E. A.; Weigel, Andrew R.; Abbott, Matthew P.; Gallo, Robert M.; Mitton, Adam A.; Klumpp, Douglas A.

doi:10.1021/jo802798x

Cited by 31 publications

(12 citation statements)

References 30 publications

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“…Then reactions of compounds 5 and 6 with arenes in TfOH were checked. Analogously to other heteroaromatic aldehydes of the series of pyridine [ 19 ], quinolone [ 20 ], pyrazol [ 21 ], and imidazole [ 22 ], the superelectrophilic activation of the formyl group in 5 was expected. Indeed, compounds 5a , b and d reacted with benzene in a Friedel–Crafts process affording N- diphenylmethyl substituted derivatives 7a–c , respectively ( Scheme 3 ).…”

Section: Resultsmentioning

confidence: 99%

Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

Gurskaya

Belyanskaya

Ryabukhin

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe reaction of 3-aryl-N-(aryl)propiolamides with arenes in TfOH at room temperature for 0.5 h led to 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones in yields of 44–98%. The obtained dihydroquinolinones were further transformed into the corresponding N-acyl or N-formyl derivatives. For the latter, the superelectrophilic activation of the N-formyl group by TfOH in the reaction with benzene resulted in the formation of N-(diphenylmethyl)-substituted dihydroquinolinones.

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Section: Resultsmentioning

confidence: 99%

Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

Gurskaya

Belyanskaya

Ryabukhin

et al. 2016

Beilstein J. Org. Chem.

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“…Previously superelectrophilic activation of aldehyde groups was achieved for heteroaromatic aldehydes [34–37], substituted benzaldehydes and o -phthalic dicarboxaldehyde [38]. Based on these findings, one would expect the activation of an aldehyde group of 5-HMF and 2,5-DFF, and its participation in the hydroxyalkylation of arenes.…”

Section: Introductionmentioning

confidence: 99%

Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

Ryabukhin¹,

Zakusilo

Kompanets³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe reaction of 5-hydroxymethylfurfural (5-HMF) with arenes in superacidic trifluoromethanesulfonic acid (triflic acid, TfOH) as the solvent at room temperature for 1–24 h gives rise to 5-arylmethylfurfurals (yields of 17–91%) and 2-arylmethyl-5-(diarylmethyl)furans (yields of 10–37%). The formation of these two types of reaction products depends on the nucleophilicity of the arene. The same reactions under the action of acidic zeolites H-USY in high pressure tubes at 130 °C for 1 h result in the formation of only 5-arylmethylfurfurals (yields of 45–79%). 2,5-Diformylfuran (2,5-DFF) in the reaction with arenes under the action of AlBr3 at room temperature for 1 h leads to 5-(diarylmethyl)furfurals (yields of 51–90%). The reactive protonated species of 5-HMF and 2,5-DFF were characterized by NMR spectroscopy in TfOH and studied by DFT calculations. These reactions show possibilities of organic synthesis based on biomass-derived 5-HMF and 2,5-DFF.

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“…This ring system is present in important biological building blocks, such as histidine and histamine. It has been reported that imidazole and its analogues inhibit the proliferation of melanoma cells [4,5] . Recently, several studies have revealed that cimetidine (a histamine‐2 (H 2 ) receptor antagonist), imidazo[1,2‐ a ]quinoxaline and imidazo[1,5‐ a ]quinoxaline (analogues of imiquimod) exhibit potent anticancer activity in vitro and in vivo [6–8] .…”

Section: Introductionmentioning

confidence: 99%