The reaction of vinyl ethers with acridine

Takano, R.; Ishihara, Yoshimi; Saito, Hiroshi; Kitahara, Takio; Takano, Jiro

doi:10.1002/jhet.5570330465

Cited by 3 publications

(3 citation statements)

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“…To assess the relative reactivity of these acridine borenium salts toward other soft nucleophiles, 1,1-diphenylethylene was utilized, due to the precedence for reaction of acridine/[ 2 ] + mixtures with vinyl ethers at the C9 position (vinyl ethers themselves are not compatible with highly electrophilic borocations). 21 1,1-Diphenylethene was added to a mixture of [ 5 ][AlCl 4 ] and DBP in DCM, which caused a rapid color change from orange to dark green. Analysis of the green solution by 1 H NMR spectroscopy revealed the formation of a new product displaying a coupled AB doublet system (δ( 1 H) 6.01 and 5.00 ppm (d, 3 J HH = 10 Hz)), suggesting the formation of a new alkene-based product.…”

Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

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N-Heterocycle-Ligated Borocations as Highly Tunable Carbon Lewis Acids

et al. 2017

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The relative (to BEt3) hydride ion affinity (HIA) of a series of acridine borenium salts has been calculated, with some HIAs found to be similar to that for [Ph3C]+. The HIA at the acridine C9 position is controlled by both acridine and the boron substituents, the latter presumably affecting the strength of the B=N bond in the acridane-BY2 products from hydride transfer. Through a range of hydride abstraction benchmarking reactions against organic hydride donors the experimental HIA of [F5acr-BCat]+ (cat = catechol, F5acr = 1,2,3,4,7-pentafluoroacridine) has been confirmed to be extremely high and closely comparable to that of [Ph3C]+. The high HIA of [F5acr-BCat]+ enables H2 and alkene activation in a FLP with 2,6-di-tert-butylpyridine. Finally, the HIA of pyridine and quinoline borenium cations has been determined, with the HIA at boron in [PinB(amine)]+ (pin = pinacol, amine = pyridine or quinoline) found to be relatively low. This enabled the hydroboration of pyridine and quinoline by HBPin to be achieved through the addition of 5–10 mol % of bench-stable cationic carbon Lewis acids such as 2-phenyl-N,N-dimethylimidazolium salts.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

N-Heterocycle-Ligated Borocations as Highly Tunable Carbon Lewis Acids

et al. 2017

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“…Acheson et al and Hamana et al studied the reactions of pyridine and quinoline N-oxide compounds with nucleophilic reagents in solution [1][2][3][4][5][6][7]. Also mixtures of acridine and various vinyl ethers in methanol under reflux conditions have been shown to produce dihydroacridinyl derivatives [8].…”

Section: Introductionmentioning

confidence: 99%

Reaction of acridine with pyrazolone derivatives

Ishihara

Ito

Saito

et al. 2005

Journal of Heterocyclic Chem

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A mixture of acridine and a pyrazolone derivative was reacted in the solid state (without solvent). It is proposed that the enol tautomer (the C4-position) of the pyrazolone derivative attacks the C9-position of acridine through a nucleophilic reaction resulting in products where the C4-position of pyrazolone is connected to the C9-position of acridine. When the reaction of 3-methyl-1-phenyl-5-pyrazolone and acridine was carried out at low temperature (25°-50°), the reaction product was obtained even when the majority of the reaction mixture had not melted. The same reaction was also carried out in the presence of an ultrasonic wave at same temperature (25°-50°) and the reaction product was obtained in high yield. Under ultrasonic conditions, the reaction mixture was not melted. However, the interface between 3-methyl-1-phenyl-5-pyrazolone and acridine gradually changed from white to black. In this reaction, the dihydroacridine dimer is not obtained.

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