• Journal of the Korean Chemical Society
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• v.55 no.3
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• pp.346-353
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• 2011

Base hydrolysis of 7-hydroxy-2H-chromen-2-one (HC) and 7-hydroxy-2H-chromen-2-one-4-acetic acid (HCA) in aqueous-methanol and aqueous-acetone mixtures were studied kinetically at temperature range from 283 to 313 K. The activation parameters of the reactions were evaluated and discussed. Moreover, the change in the activation energy barrier of the investigated compounds from water to water-methanol and water-acetone mixtures was estimated from the kinetic data. It is observed that the change in activation barriers is more or less the same for the hydrolysis of HC and HCA. Base hydrolysis of HC and HCA follows a rate law with $k_{obs}=k_2[OH^-]$. The decrease in the rate constants of HC and HCA as the proportion of methanol or acetone increases is due to the destabilization of $OH^-$ ion. The high negative values of entropy of activation support the proposal mechanism, i.e. the investigated reaction takes place via the formation of an intermediate complex. Moreover, these values refer to the rigidity and stability of the intermediate complex. Thus, the ring opening of the intermediate complex would be the rate controlling step.

• Journal of the Korean Chemical Society
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• v.57 no.5
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• pp.612-617
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• 2013

The versatile, hitherto unreported 3-(4-(2-phenyldiazenyl)-2-oxo-2H-chromen-3-yl)-3-oxopropanenitrile 3 was prepared by two convenient routes: either by the reaction of ethyl 4-(2-phenyldiazenyl)-2-oxo-2H-chromen-3-carboxylate 2 with acetonitrile in the presence of sodium hydride or by treatment of 4-(2-phenyldiazenyl)-3-(2-bromoacetyl)-2H-chromen-2- one 5 with potassium cyanide. Reaction of 3 with heterocyclic diazonium salts 6, 7, 14 and 17 furnished the corresponding hydrazones 8, 9, 15 and 18. The latter hydrazones underwent intramolecular cyclization into the corresponding pyrazolo[5,1- c]-1,2,4-triazine 10, 1,2,4-triazolo[5,1-c]-1,2,4-triazine 11, 1,2,4-triazino[4,3-b]indazole 16 and imidazo[2,1-c]-1,2,4-triazine 19 derivatives, respectively upon refluxing in pyridine.

• Bulletin of the Korean Chemical Society
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• v.32 no.10
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• pp.3752-3755
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• 2011

• Journal of Integrative Natural Science
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• v.9 no.2
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• pp.94-102
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• 2016

The crystal structure of the potential active 6-ethoxy-3-phenyl-5a,9a-dihydro-3H-chromen[4,3-c][1,2]oxazole-3a(4H)-carbonitrile ($C_{19}H_{15}N_2O_3$) has been determined from single crystal X-ray diffraction technique. The title compound crystallizes in the monoclinic space group C2/c with unit cell dimension a= 29.3026(9) ${\AA}$, b= 6.7695(2) ${\AA}$ and c= 19.7597(6) ${\AA}$ [${\alpha}= 90^{\circ}$, ${\beta}= 125.709(10)^{\circ}$ and ${\gamma}= 90^{\circ}$]. Single crystals suitable for X-ray diffraction were obtained by slow evaporation method, the isoxazole and six membered pyran rings adopts envelope conformation. The crystal packing of the molecules is stabilized by the weak $C-H{\ldots}N$ hydrogen bond interaction.

• Journal of Integrative Natural Science
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• v.9 no.2
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• pp.103-112
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• 2016

The crystal structure of the potential active Methyl 8-bromo-3-phenyl-5a,9a-dihydro-3H-chromen [4,3-c][1,2] isoxazole-3a(4H)-carboxylate ($C_{18}H_{15}BrNO_4$) has been determined from single crystal X-ray diffraction technique. The title compound crystallizes in the triclinic space group Pī with unit cell dimension a=8.3129 (3) ${\AA}$, b=9.5847 (4) ${\AA}$ and c=11.1463(4) ${\AA}$ [${\alpha}=98.457(3)^{\circ}$, ${\beta}=102.806(2)^{\circ}$ and ${\gamma}=105.033(5)^{\circ}$]. Single crystals suitable for X-ray diffraction were obtained by slow evaporation method, the isoxazole and six membered pyran rings adopts envelope conformation. In the crystal, molecules are linked via pairs of inter molecular $C-H{\ldots}O$ hydrogen bonds to form dimmers.

• Bulletin of the Korean Chemical Society
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• v.35 no.6
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• pp.1670-1674
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• 2014

Two red emitters, 2-(7-(4-(diphenylamino)styryl)-2-methyl-4H-chromen-4-ylidene)malonitrile (Red 1) and 2-(7-(julolidylvinyl)-2-methyl-4H-chromen-4-ylidene)malonitrile (Red 2) have been designed and synthesized for application as red-light emitters in organic light emitting diodes (OLEDs). In these red emitters, the julolidine and triphenyl moieties were introduced to the emitting core as electron donors, and the chrome-derived electron accepting groups such as 2-methyl-(4H-chromen-4-ylidene)malononitrile were connected to electron donating moieties by vinyl groups. To explore the electroluminescence properties of these materials, multilayered OLEDs using red materials (Red 1 and Red 2) as dopants in $Alq_3$ host were fabricated. In particular, a device using Red 1 as the dopant material showed maximum luminous efficiencies and power efficiencies of 0.82 cd/A and 0.33 lm/W at $20mA/cm^2$. Also, a device using Red 2 as a dopant material presented the CIEx,y coordinates of (0.67, 0.32) at 7.0 V.

• Bulletin of the Korean Chemical Society
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• v.31 no.3
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• pp.664-669
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• 2010

This paper describes a new synthetic approach for biologically interesting geranylated acetophenones. The first total syntheses of 1-(5-geranyloxy-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone and 1-[5-geranyloxy-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl]ethanone, isolated from Melicope semecarpifolia, were carried out starting from commercially available 2,4,6-trihydroxyacetophenone.

• Bulletin of the Korean Chemical Society
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• v.30 no.12
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• pp.2969-2972
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• 2009

A mild and efficient method has been developed for condensation of substituted phenol with ${\beta}$-ketoester in the presence of catalytic amount of ammonium metavanadate (10 mol%) at ambient temperature to afford the corresponding substituted 4-methyl-2H-chromen-2-one in high yields under mild conditions. Utilization of commercially available inexpensive catalyst makes this manipulation very interesting from an economic perspective.

• Journal of Pharmacopuncture
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• v.11 no.1
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• pp.177-187
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• 2008

Objectives : This study was performed to analyze the effective components of essential oil obtained from Yongdamsagantang, which has been efficacious against leukorrhea in gynecologic diseases. Methods : I obtained the essential oils of Yongdamsagan-tang by hydrodistillation extraction method and supercritical fluid extraction(SFE) method, and then I analyzed those by GC/MS(Gas Chromatography/Mass Spectrum). Results : 1. The optimum SFE(Supercritical Fluid Extraction) condition was obtained in the following experiment conditions: pressure 200atm, temperature $45^{\circ}C$, duration of extraction 25minutes. 2. With GC(Gas Chromatography) and GC/MS(Gas Chromato- graphy/Mass Spectrum) analysis, I identified 37 compounds in the Yongdamsagan-tang's essential oil obtained through the SFE method. The main compounds were as follows : 3-Methyl-but-2-enoic acid,2,2-dimethyl-8-oxo-3,4-dihydro-2H,8H -pyrano[3,2-g]chromen-3-yl ester(49.81%), (Z)-6-Pentadecen-1 -ol(3.19%), (-)-Spathulenol(2.40%). 3. I identified 4 compounds in the Yongdamsagan-tang's essential oil obtained through the hydrodistillation method. The main compounds were as follows : 3-Methyl-but-2-enoic acid, 2,2-dimethyl-8-oxo-3,4-dihydro-2H,8H-pyrano [3,2-g]chromen-3-yl ester(2.61%). 4. 3-Methy I-but-2-enoic acid, 2,2-dimethyl-8-oxo-3,4-dihydro-2H,8H-pyrano[3,2-g] chromen-3-yl ester, all were identified in both the SFE method and the hydrodistillation method, but the others were not identified in common. 5. I also conducted an additional test in order to examine the essential oil's antimicrobial action against bacteria. Both MIC(Minimum Inhibitory Concentrations) and MBC(Minimum Bactericidal Concentrations) were $0.125mg/m{\ell}$ against N. meningitidis, however MIC and MBC were $1.0mg/m{\ell}$ in antimicrobial action against 12 different genera of bacteria.

• Archives of Pharmacal Research
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• v.29 no.10
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• pp.840-844
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• 2006

For the exploration of pharmacophoric moiety of malloapelta B (1) possessing the inhibitory activity of $NF-{\kappa}B$ activation, structural variation of ${\alpha},{\beta}-unsaturated$ carbonyl motif was attempted. 1 was reduced by catalytic hydrogenation, sodium borohydride, and lithium aluminumhydride. Catalytic hydrogenation with 30 psi or 15 psi of $H_2$ gas of 1 generated 8-butyl-5,7-dimethoxy-2,2-dimethylchroman (2) and 1-(5,7-dimethoxy-2,2-dimethylchroman-8-yl)butan-1-one (3), respectively. Reduction with sodium borohydride occurred at the double bond of ${\alpha},{\beta}-unsaturated$ ketone of 1 to give 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)butan-1-one (4). Reduction of 1 with lithium aluminumhydride and then quenched with methanol and water produced unexpected products, 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-3-methoxy-1-butene (5) and 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-3-hydroxy-1-butene (6). These are formed from the isomerization of initial product 9 through the continuous conjugate carbocation intermediate 11. Addition of ethylmagnesium bromide and dimethyl malonate anion to 1 gave the conjugate adducts 7 and 8. Ethylmagesium bromide and sodium borohydride reduction unusually gave the conjugate addition due to steric congestion around carbonyl group of 1. Compound 2 exhibits the reduced inhibitory activity against $NF-{\kappa}B$ activation and the others do not show the activity. Therefore ${\alpha},{\beta}-unsaturated$ carbonyl group of 1 should be important for its inhibitory activity.