Synthesis of Heterocyclic Compounds via Nucleophilic Aroylation Catalyzed by Imidazolidenyl Carbene

Suzuki, Yumiko; Toyota, Tomonori; Miyashita, Akira; Sato, Masayuki

doi:10.1248/cpb.54.1653

Cited by 26 publications

(15 citation statements)

References 41 publications

(43 reference statements)

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“…The second one involves the cyclodehydration of o-phenoxy benzoic acids [15][16][17]. Recently, synthesis has also been conducted via N-heterocyclic carbene catalyzed nucleophilic aroylation [18]. Various types of catalysts are also used for cyclization reactions to form xanthone core, such as NaH/CsF/THF [19], NaOC 2 H 5 /Cu/Cu 2 O [20], ZnCl 2 /POCl 3 [21], AlCl 3 /anhydrous ether [22,23], Pd (PPh3)4/K 2 CO 3 /acetone [24].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis, Antioxidant Activity and Toxicity Evaluation of Some Hydroxyxanthones

Yuanita¹,

Pranowo²,

Siswanta³

et al. 2018

ChChT

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Some new hydroxyxanthone compounds were prepared through one pot cyclodehydration reaction of hydroxybenzoic acid derivatives (salicylic acid or resorcylic acid) with phloroglucinol or pyrogallol in the presence of Eaton's reagent (P 2 O 5 /MeSO 3 H). The synthesized compounds were screened for their antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH) methods to determine their inhibitory concentration (IC 50). Cytotoxicity of the prepared compounds was also evaluated by MMT assay on Vero cell line. It was observed that the position and the number of hydroxyl groups could significantly affect the potent antioxidant activity of the prepared compounds. Cytotoxicity evaluation of new compounds indicated that the synthesized series of hydroxyl xanthone were categorized as very strong antioxidants and showed potential development as a commercial antioxidant compound.

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Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis, Antioxidant Activity and Toxicity Evaluation of Some Hydroxyxanthones

Yuanita¹,

Pranowo²,

Siswanta³

et al. 2018

ChChT

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“…[17][18][19][20] Research to further characterize these compounds has been increasing in the past few years.…”

Section: Introductionmentioning

confidence: 99%

A Combined Experimental and Computational Thermodynamic Study of Difluoronitrobenzene Isomers

et al. 2010

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This work reports the experimental and computational thermochemical study performed on three difluorinated nitrobenzene isomers: 2,4-difluoronitrobenzene (2,4-DFNB), 2,5-difluoronitrobenzene (2,5-DFNB), and 3,4-difluoronitrobenzene (3,4-DFNB). The standard (p° = 0.1 MPa) molar enthalpies of formation in the liquid phase of these compounds were derived from the standard molar energies of combustion, in oxygen, at T = 298.15 K, measured by rotating bomb combustion calorimetry. A static method was used to perform the vapor pressure study of the referred compounds allowing the construction of the phase diagrams and determination of the respective triple point coordinates, as well as the standard molar enthalpies of vaporization, sublimation, and fusion for two of the isomers (2,4-DFNB and 3,4-DFNB). For 2,5-difluoronitrobenzene, only liquid vapor pressures were measured enabling the determination of the standard molar enthalpies of vaporization. Combining the thermodynamic parameters of the compounds studied, the following standard (p° = 0.1 MPa) molar enthalpies of formation in the gaseous phase, at T = 298.15 K, were derived: Δ(f)H(m)° (2,4-DFNB, g) = -(296.3 ± 1.8) kJ · mol⁻¹, Δ(f)H(m)° (2,5-DFNB, g) = -(288.2 ± 2.1) kJ · mol⁻¹, and Δ(f)H(m)° (3,4-DFNB, g) = -(302.4 ± 2.1) kJ · mol⁻¹. Using the empirical scheme developed by Cox, several approaches were evaluated in order to identify the best method for estimating the standard molar gas phase enthalpies of formation of these compounds. The estimated values were compared to the ones obtained experimentally, and the approach providing the best comparison with experiment was used to estimate the thermodynamic behavior of the other difluorinated nitrobenzene isomers not included in this study. Additionally, the enthalpies of formation of these compounds along with the enthalpies of formation of the other isomers not studied experimentally, i.e., 2,3-DFNB, 2,6-DFNB, and 3,5-DFNB, were estimated using the composite G3MP2B3 approach together with adequate gas-phase working reactions. Furthermore, we also used this computational approach to calculate the gas-phase basicities, proton and electron affinities, and, finally, adiabatic ionization enthalpies.

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“…Other solvents, such as dioxane, ClCH 2 CH 2 Cl, CH 3 CN, THF, dimethoxyethane, and glycol were unsuccessful in this reaction with no desired product obtained (see Table S1, entries [9][10][11][12][13][14]. N,Ndimethylacetamide (DMA), N,N-dimethylformamide (DMF), and toluene were applicable.…”

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confidence: 99%

“…Good yields were generally achieved for substrates 1 j-1 l. 4-Methoxyl and 4-cyano-substituted substrates 1 m and 1 n also efficiently provided the desired products (Table 2, entries [13][14]. Good yields were generally achieved for substrates 1 j-1 l. 4-Methoxyl and 4-cyano-substituted substrates 1 m and 1 n also efficiently provided the desired products (Table 2, entries [13][14].…”

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confidence: 99%

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Transition‐Metal‐Free Synthesis of Acridones via Base‐Mediated Intramolecular Oxidative C−H Amination

et al. 2018

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Synthesis of Heterocyclic Compounds via Nucleophilic Aroylation Catalyzed by Imidazolidenyl Carbene

Cited by 26 publications

References 41 publications

One-Pot Synthesis, Antioxidant Activity and Toxicity Evaluation of Some Hydroxyxanthones

One-Pot Synthesis, Antioxidant Activity and Toxicity Evaluation of Some Hydroxyxanthones

A Combined Experimental and Computational Thermodynamic Study of Difluoronitrobenzene Isomers

Transition‐Metal‐Free Synthesis of Acridones via Base‐Mediated Intramolecular Oxidative C−H Amination

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