• Bulletin of the Korean Chemical Society
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• v.32 no.2
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• pp.635-638
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• 2011

A simple and efficient method for the synthesis of $\beta$-amino carbonyl compounds by one-pot three-component Mannich reaction of acetophenone, aromatic aldehydes and aromatic amines using a carbon-based solid acid (CBSA), as an effective and reusable catalyst, is described. The present methodology offers several advantages such as simple procedure with an easy work-up, shorter reaction times, and high yields.

• Bulletin of the Korean Chemical Society
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• v.32 no.5
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• pp.1703-1708
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• 2011

ZSM-5-$SO_3H$ efficiently catalyzed the one-pot three-component Mannich reaction of aldehydes, anilines, and ketones. ${\beta}$-Aminocarbonyl compounds were obtained in reasonable yields and excellent stereoselectivities when the reaction was carried out at room temperature under solvent-free conditions. Simple experimental conditions and product isolation procedure makes this protocol potential for the development of clean and environment-friendly strategy for the synthesis of ${\beta}$-amino-ketones. The catalyst was recovered and reused for subsequent runs.

• Journal of the Korean Chemical Society
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• v.55 no.4
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• pp.644-649
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• 2011

Polyaniline/$SiO_2$ catalyzed one-pot mannich reaction of acetophenone, aromatic aldehydes and aromatic amines are carried out in ethanol to afford various ${\beta}$-amino ketones. The various wt% of polyaniline were supported on pure silica synthesized by using chemical oxidative method. The catalyst prepared has been characterized by means of thermal analysis (TG-DTA), X-ray diffraction (XRD), scanning electron microscopy (SEM) energy dispersive spectroscopy (EDS), and Fourier transform infrared spectroscopy (FT-IR). Solvent stability of catalyst was tested using UV-Visible spectroscopy. This protocol has several advantages such as high yield, simple work up procedure, non-toxic, clean, easy recovery and reusability of the catalyst.

• Bulletin of the Korean Chemical Society
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• v.30 no.7
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• pp.1437-1438
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• 2009

• Bulletin of the Korean Chemical Society
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• v.11 no.1
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• pp.22-25
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• 1990

The condensation of 1-amino-1,2-dihydro-3,6-pyridazinedione (1) and 2-amino-2,3-dihydro-1,4-phthalazinedione (2) with mesityl oxide or 3-penten-2-one in acetic acid-ethanol (1:1) gave 3,4,6,9-tetrahydro-6,9-dioxopyridazino[1,2-a][1,2, 3]triazines (9,11) and 3,4,6,11-tetrahydro-6,11-dioxo[1,2,3]triazino[1,2- b]phthalazines (10,12), respectively. The condensation of 1 and 2 with crotonaldehyde, cinnamaldehyde or acrylaldehyde under the same reaction condition gave only N-alkylidene derivatlives (3-8). When the N-alkylidene derivatives isolated from the reaction of 1 and 2 with crotonaldehyde and cinnamaldehyde (3-6) were refluxed in acetic acid, the corresponding heterocyclic compounds (13-16) were obtained.

• Archives of Pharmacal Research
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• v.27 no.6
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• pp.604-609
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• 2004

A new indolinepeptide (3） was isolated, together with two known compounds, a cerebroside (1） and an alloxazine (2）, from silkworm larvae infected with Paecilomyces sp. J300. On the basis of spectroscopic data, their structures were elucidated as (4E, 8E, 25, 2＇R, 3R ）-N-2＇-hydroxy-hexadecanoyl-1-O-$\beta$-D-glucopyranosyl-9-methyl-4, 8-sphingadienine (1）, 7,8-dimethylalloxazine (2） and 3$\beta$,5-dihydroxy-1-N-methyl-indoline-2$\beta$-carbonyl amino-D-alanyl-erythro-$\beta$-hydoxyiso-leucinyl-glycine (3）.

• BMB Reports
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• v.32 no.4
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• pp.370-378
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• 1999

The effects of carnosine and related compounds (CRC) including anserine, homocarnosine, histidine, and ${\beta}$-alanine, found in most mammalian tissues, were investigated on in vitro glucose oxidation and glycation of human serum albumin (HSA). Carnosin and anserine were more reactive with D-glucose than with L-lysine. In the presence of $10\;{\mu}M$ Cu (II), although carnosine and anserine at low concentrations effectively inhibited formation of ${\alpha}$-ketoaldehyde from D-glucose, they increased generation of $H_2O_2$ in a dose-dependent manner. Carnosine, homocarnosine, anserine, and histidine effectively inhibited hydroxylation of salicylate and deoxyribose degradation in the presence of glucose and $10\;{\mu}M$ Cu (II). In the presence of 25 mM D-glucose, copper and ascorbic acid stimulated carbonyl formation from HSA. Except for ${\beta}$-alanine, CRC effectively inhibited the copper-catalyzed carbonyl formation from HSA. The addition of 25 mM D-glucose and/or $10\;{\mu}M$ Cu (II) to low density lipoprotein (LDL) increased formation of conjugated dienes. CRC effectively inhibited the glucose and/or copper-catalyzed LDL oxidation. CRC also inhibited glycation of HSA as determined by hydroxymethyl furfural and lysine with free ${\varepsilon}$-amino group. These results suggest that CRC may play an important role in protecting against diabetic complications by reacting with sugars, chelating copper, and scavenging free radicals.

• Journal of the Korean Chemical Society
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• v.33 no.4
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• pp.426-430
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• 1989

Amino alcohol-derived thiazolidinethiones [4-(S)-IPTT, 4(S)-ETT] serve as efficient chiral auxiliary in tin medicated aldol condensation. A highly enantioselective aldol-type reaction forming various ${\beta}$-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehyde is achieved via divalent tin enolate. The other advantages of these chiral auxiliaries were the ease of removal by methanolysis.

• Korean Journal of Food Science and Technology
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• v.34 no.4
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• pp.604-609
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• 2002

The sensory properties and flavor components of the white bread added with arrowroot juice. The lightness of bread crumb decreased significantly as arrowroot juice was added. While the yellowness increased slightly, redness increased remarkably. The hardness, chewiness and adhesiveness of the white bread added with arrowroot juice increased more than those of the control bread, but they had no statistical significance. While the gumminess increased significantly and springiness decreased significantly, the cohesiveness did not indicate significant differences among the comparison groups. In sensory evaluation, the texture, flavor and sweetness did not indicate significant difference among the comparison groups, while the color and overall acceptability indicated significant difference. The optimum concentration of arrowroot juice in the white bread was 25% based on the sensory evaluation scores. The main flavors components of the white bread added with 25% arrowroot juice were compounds translated by arrowroot juice and the compounds formed by amino-carbonyl reaction. The translated flavors were methoxy phenol, ${\beta}-damascenone$, benzylcyanide, and menthofuran. The compounds formed by amino-carbonyl reaction were alkyl pyrazines, pyrroles and furans.

• Clean Technology
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• v.29 no.2
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• pp.79-86
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• 2023

The homogeneous catalyst, Ru-MACHO-BH, selectively performs hydrogenation reactions only on the carbonyl group of α, β-unsaturated aldehyde compounds with extremely high reactivity and selectivity. However, the hydrogenation of α, β-unsaturated aldehydes involves a heterogeneous Diels-Alder reaction, resulting in the formation of significant amounts of byproducts, such as dimers. In this study, we used the Ru-MACHO-BH catalyst (Carbonyl hydrido (tetrahydroborato) [bis (2-diphenyl phosphino ethyl) amino] ruthenium(II)) to selectively hydrogenate the carbonyl group of a specific type of α, β-unsaturated aldehyde called methacryl aldehyde, leading to the synthesis of methallyl alcohol. Simultaneously, we applied diols to inhibit the formation of byproducts. The results demonstrate that monoethylene glycol can significantly reduce the formation of diols. Based on these results, we effectively suppressed the formation of dimers containing vinyl groups in methacryl aldehyde by using hydroquinone, which can efficiently inhibit the chemical interaction of vinyl groups. Consequently, the conversion rate of methacryl aldehyde was increased. Ultimately, by reducing the amount of the expensive homogeneous catalyst Ru-MACHO-BH to 1/10, we achieved a selectivity of over 90% and a yield of over 80% for the desired product, methallyl alcohol. These results provide a method to minimize yield reduction while reducing the usage of expensive catalysts, thereby improving cost-effectiveness. We expect that the reaction could be applied to various kinds of selective hydrogenation and has been successfully run on an industrial scale.