• Bulletin of the Korean Chemical Society
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• 제13권2호
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• pp.184-187
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• 1992

Regeneration methods of oximes, hydrazones, and N,N-dimethylhydrazones to the related carbonyl compounds were effected using various dicarbonyl compounds which are activated with electron withdrawing substituents such as trifluoromethylated $\beta-diketones$, $\beta-acylpyruvates$, and $\alpha-diketones$ via an equilibrium exchange reaction. The chemical transformations of the dicarbonyl compounds in the exchange reaction were investigated by various spectroscopic methods.

• Bulletin of the Korean Chemical Society
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• 제32권5호
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• pp.1697-1702
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• 2011

A facile, green, efficient and environment-friendly protocol for the synthesis of 14-aryl- or alkyl-14Hdibenzo[a,j]xanthene, 1,8-dioxooctahydroxanthene and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one have been developed by one-pot condensation of various aldehydes with (i) ${\beta}$-naphthol (ii) cyclic 1,3-dicarbonyl compounds and (iii) ${\beta}$-naphthol and cyclic 1,3-dicarbonyl compounds, in the presence of 1,3,5-trichloro-2,4,6-triazinetrion (trichloroisocyanuric acid, TCCA) as catalyst under solvent-free conditions. The present approach offers the advantages of clean reaction, simple methodology, short reaction time, easy purification, and economic availability of the catalyst.

• Bulletin of the Korean Chemical Society
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• 제29권6호
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• pp.1195-1198
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• 2008

Kinetic studies of the additions of benzylamines to a noncyclic dicarbonyl group activated olefin, methyl $\alpha$-acetyl-$\beta$ -phenylacrylates (MAP), in acetonitrile at 30.0 ${^{\circ}C}$ are reported. The rates are lower than those for the cyclic dicarbonyl group activated olefins. The addition occurs in a single step with concurrent formation of the $C_\alpha$ -N and $C_\beta$ -H bonds through a four-center hydrogen bonded transition state. The kinetic isotope effects ($k_H/k_D$ > 1.0) measured with deuterated benzylamines ($XC_6H_4CH_2ND_2$) increase with a stronger electron acceptor substituent ($\delta\sigma$ X > 0) which is the same trend as those found for other dicarbonyl group activated series (1-4). The sign and magnitude of the cross-interaction constant, ρXY, is comparable to those for the normal bond formation processes in the $S_N2$ and addition reactions. The relatively low ${\Delta}H^\neq$ and large negative ${\Delta}S^\neq$ values are also consistent with the mechanism proposed.

• Journal of Photoscience
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• 제2권2호
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• pp.73-76
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• 1995

The photohydration of 1-(m-nitrophenyl)-5, 5-dimethyl-1, 3-hexadiyne (m-NDHD) affords allenyl ketone compound (1) via triplet excited state which is converted into $\beta$-dicarbonyl compound (2) through thermal hydration. The allenyl ketone is formed by the synchronous addition of water with protonation at C$_1$ indicating that m-NDHD has the reverse polarization and greater electron withdrawing effect in the triplet excited state in comparison with p-NDHD.

• Bulletin of the Korean Chemical Society
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• 제23권7호
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• pp.998-1002
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• 2002

An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of $\alpha\beta-unsaturated$, aldehydes in moderate yields. This method has been applied to the synthesis of pyranocoumar ins, pyranophenalenones, and pyranoquinolinone alkaloids.

• Rapid Communication in Photoscience
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• 제1권1호
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• pp.17-18
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• 2012

Photoaddition reactions between 1,2-dicarbonyl compounds and silyl enol ethers in acetonitrile and benzene were explored. Irradiation of acetonitrile or benzene solutions containing 1,2-diketone, acenaphthalquinone, phenanthrene-quinone and silyl enol ethers is observed to promote the production of 1,4-dioxenes, oxetanes, and ${\beta}$-hydroxyketone by the [4+2]-cycloadditon, Paterno-Buchi processes, and SET promoted Claisen-type condensation. Among these competitive pathways leading to the generation of each types of products, SET promoted 1,4-dioxene and ${\beta}$-hydroxyketone formation are more favored regardless of solvent polarity.

• Bulletin of the Korean Chemical Society
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• 제32권5호
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• pp.1543-1546
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• 2011

N-Bromosaccharin/$Mg(ClO_4)_2$ is an effective and regioselective system for ${\alpha}$-monobromination of 1,3-dicarbonyl compounds. A wide variety of ${\beta}$-keto esters and 1,3-diketones in reaction with this system afforded a regioselectively ${\alpha}$-monobrominated products. The bromination reaction can be conducted at 0-5 $^{\circ}C$ either in solution or under solvent-free conditions.

• Bulletin of the Korean Chemical Society
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• 제31권11호
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• pp.3238-3240
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• 2010

A new and efficient method for the preparation of substituted 3,4-dihydropyrimidin-2(1H)-ones via Biginelli synthesis using catalytic amounts of 1,3-dichloro-5,5-dimethylhydantoin is presented. Short reaction times, easy work-up, high yields of products and stability, easy-handling, non-toxicity and cheapness of the catalyst are noteworthy advantages of the present work.

• Bulletin of the Korean Chemical Society
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• 제29권9호
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• pp.1752-1754
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• 2008

A simple and efficient synthesis of 3,4-dihydropyrimidinones or thiones is described, using silica-supported perchloric acid ($HClO_4-SiO_2$) as a heterogeneous catalyst from an aldehyde, $\beta$-dicarbonyl compound, and urea or thiourea under solvent-free conditions. Compared to the classical Biginelli reactions, this method consistently has the advantage of high yields, short reaction time, easy separation, and tolerance towards various functional groups.

• 한국수산과학회지
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• 제19권1호
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• pp.45-51
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• 1986

D-glucose-glycine 계를 사용하여 Maillard 반응에 의하여 생성되는 저분자 휘발성성분을 비롯하여 amide 화합물의 생성 및 그 기구를 검토하였다. 그 결과, 동정된 저분자 휘발성성분 중에서, headspace gas 중의 휘발성성분은 furan, acetone, 2-methylfuran, 2,5-dimethylfuran 2-butanone 2,3-pentanedione, diacetyl 등이었다, 이 중에서 diacetyl의 생성량이 가장 많아, 전 peak 면적의 약 $70\%$를 차지하였다. 또한, 에테르 추출물중의 주요반응생성물은 초산, furfuryl alcohol 2,5-dimethylpyrrole 2-acetylpyrrole 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 등이었고, ethyl acetate 로 추출한 산성획분중에는 N-acetyl-glycine와 N-methylacetamide 등 2종류의 amide 화합물의 생성이 밝혀졌다. 이들 amide 화합물적 생성기구를 밝히기 위하여, Mailiard 반응초기생성물인 diacetyl 및 glyoxal을 각각 butylamine과 반응시킨 결과, Schiff 염기의 산화적 분해로 N-butylacetamide 및 N-butylformamide의 생성이 인정되었다. 따라서 N-acetylglycine 및 N-methylacetamide는 glucosylamine의 2,3-enol 화 및 ${\beta}-elimination$에 의한 탈수의 진행으로 생성된 dicarbonyl 화합물이 glycine과 반응하여 Schiff 염기를 형성하고, 이 Schiff 염기가 산화적분해를 받아서 N-acetylglycine이 생성되고, N-methylacetamide는 N-acetylglycine의 탈탄산에 의해서 생성된다고 생각한다.