• Bulletin of the Korean Chemical Society
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• 제33권1호
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• pp.55-59
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• 2012

Treatments of organic isothiocyanates (R-NCS) with $NaN_3$ in the presence of pyridine in water at room temperature gave corresponding various organic tetrazole-thiones, [$S=CN_4(R)$] (R = alkyl or aryl). Isolated products are obtained as white or yellow solids in good yields (76-97%). The molecular structure by X-ray diffraction study for one of products shows the proposed formation. In addition, one-pot synthesis of 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles has been demonstrated. Addition of alkyl or aryl halides into the mixture of organic isothiocyanates, $NaN_3$, and pyridine in water at room temperature exclusively formed 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles (S-derivatives) in high yields.

• 약학회지
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• 제47권5호
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• pp.276-282
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• 2003

For the development of new synthetic method for unnatural amino acid esters, N-aryl phenylglycine Ο-alkyl esters 4a∼i were synthesized through esterification, bromination, C-N bond formation from commercially available phenylacetic acids. An efficient and practical reaction condition for esters 2a∼c was that the starting materials 1a∼c were refluxed in absolute methanol for 3 hours with catalytic concentrated hydrosulfuric acid. In addition, bromines 3a∼c were formated for 3h in dichloromethane at rt with N-bromosuccinimide. Bromines 3a∼c were also converted to 4a∼i through substitution of arylamines during refluxing for 24 hours in ethanol with triethylamine. Interestingly, ethyl esters 5a∼c were formed via transesterification reaction when the p-sulfamylanilino group was used as a nucleophile in ethanol solvent.

• 대한화학회지
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• 제30권1호
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• pp.126-134
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• 1986

Aniline과 n-alkyl alcohol類로 부터 6-alkylbenzofuroxan을 얻고 이것과 4-aminophenol을 反應시켜 butyl, hexyl, octyl기를 가진 7-Alkyl-2-aminophenazine-5,10-dioxide를 合成하였다. 그리고 benzofuroxane과 4-aminophenol을 反應시켜 2-aminophenazine-5,10-dioxide도 合成하였다. 生成物들은 IR, NMR, 元素分析등으로 확인하였다. 이들 phenazine 誘導體의 수용액에 대한 表面張力을 測定하였는데 alkyl기의 탄소수가 증가할수록 表面張力이 底下됨을 알았다. 또한 抗菌性을 稀釋法에 의하여 調査하였는데 alkyl기의 탄소수가 4개인 butyl 誘導體의 경우가 가장 抗菌性이 강했으며, alkyl기가 없는 2-aminophenazine-5,10-dioxide보다는 alkyl기가 置換된 2-aminophenazine-5,10-dioxide의 抗菌性이 더 강하다는 것을 알았다.

• Bulletin of the Korean Chemical Society
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• 제35권9호
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• pp.2758-2764
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• 2014

We demonstrated the synthesis of organic carbonates using alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and alcohol in the presence of aluminum chloride. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates were reacted with alcohol in the presence of $AlCl_3$ in toluene at room temperature to afford the corresponding unsymmetric and symmetric organic carbonates in good to excellent yields. These are efficient and convenient processes. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates are solid, stable and non-toxic $CO_2/CO_2R$(Ar) source. It is noteworthy that the reaction is carry out under an ambient and acidic conditions, the easy-to prepare and readily available starting materials and the quantitative isolation of reusable 4,5-dichloropyridazin-3(2H)-one.

• 약학회지
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• 제7권2_3호
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• pp.58-66
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• 1963

Alkyl-phenylthionocarbamates already have been investigated as anthelmintics. Especially ethyl-phenylthionocarbamate is noted for its anthelmintic action. Author studied methods for synthesizing Alkyl-phenylthionocarbamates, Alkyl-p-phenetyl thionocarbamates, Alkyl-cyclohexylthionocarbamates, 5 kinds for each. For alkyl radical $-CH_{3}$, $-C_{2}H_{5}$, -n-propyl, -isobuthyl, -n-buthyl, being chosen. Compounds VIII, X, XIII, XIV, and XV are new compounds. At the sametime author prepared 4 kinds of Arylthionocarbamates, among which XVII, and XIX being new compounds. (Table I) The anthelmintic action of these thionocarbamates has been examined through kymographic records indicating the action of neuromuscular preparation of Eisenia foetida Savigny in the various concentration fo above compounds: -Trendelenburg method. Santonine as the criterion of the estimation. (Table. II) 1. Compounds I-X could be prepared by method A or method B. method A in sealed tube brought on better yield and purity. 2. Compounds XI-XV couldn't be prepared by method A but by method B. 3. Arylthionocarbamates XVI, XVII, XVIII, and XIX couldn't be prepared by method A or method B but by method C. 4. Analyzed N. contained in all compounds. Analyzed C.H. and N. contained in unknown compounds, VIII, X, XIII, XIV, XV, XVII, and XIX. 5. Examination of anthelmintic action has been done under the advice of Prof. J.S.Oh medical college, Seoul Nat. University. 6. Compounds VI-X showed little action. 7. Compounds XVI-XIX showed almost no action. 8. Compounds XI-XV showed stronger action than compounds I-V, which was reported already as a usable anthelmintics. 9. Compounds XI, XII, XIII and XIV showed strongest actions, stronger than santonine as recorded on kymographion of the Trendelenburg method. Provided that, the toxity of these compounds found mild enough for human system, these compounds will serve as anthelmintics of greater powers than compounds I-V. 10. In Alkylthionocarbamates, R'NH-radical more influence on the anthelmintic action than ester radical(-OR).

• Bulletin of the Korean Chemical Society
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• 제15권3호
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• pp.204-209
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• 1994

Catalytic hydroacylation has been achieved by the reaction of 8-quinolinecarboxaldehyde (1) and various vinyl derivatives such as 2a, 2b and 2c with Wilkinson's complex (3) to give linear alkyl ketones, 4a, 4b and 4c, respectively. However, stoichiometric ligand-promoted hydroacylation of 2a and 2b with [$(C_8H_{14})_2RhCl]_2$ (5) resulted in a mixture of the branched alkyl ketones and the linear alkyl ketones in different ratios. Stoichiometric hydroacylation of some other olefin derivatives such as 6, 11, 12 and 26, produced functionalized alkyl ketone compounds.

• Archives of Pharmacal Research
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• 제29권3호
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• pp.183-187
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• 2006

A series of 6-hydroxy-7-methoxy-4-oxo-4H-chromene-2-carboxylic acid N-alkyl amides (3a-g) were synthesized and their antioxidant activities were evaluated using rat brain homogenates.

• Bulletin of the Korean Chemical Society
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• 제17권5호
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• pp.437-442
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• 1996

Electrocyclic ring-closure of 6-vinylcyclohepta-1,3,5-isocyanate has been carried out in the presence of triphenylphosphine to examine a catalyzing effect of the triphenylphosphine. The preparation of 10-(1-carboalkoxyalkyl)-2,7-methanoaza[10]annulenes by the electrocyclic ring-closure of ketenimine intermediates, which are formed by the reaction of triphenylalkylidenephosphorane and 6-vinylcyclo-hepta-1,3,5-isocyanate, is described. 10-Alkyl-2,7-methanoaza[10]annulenes were prepared by basic hydrolysis of the carboalkoxyaza[10]annulenes and decarboxylation of the acid intermediates. In the same manner, 10-(N-alkyl(or aryl))-2,7-methanoaza[10]annulenes were prepared from the reaction of the isocyanate and N-alkyl(or aryl)iminotriphenylphosphorane via electrocylic ring-closure of carbodiimide intermediate.

• 대한화장품학회지
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• 제30권4호
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• pp.491-497
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• 2004

일련의 Alkyl-3,4-dihydroxybenzoate (A)와 N-Alkyl-3,4-dihydroxybenzamide (B) 유도체들의 치환기($R_l$ 및 $R_2$) 변화에 따른 멜라닌생성 저해활성 관계들을 HQSAR 방법으로 분석하였다. 멜라닌생성 저해활성에 관하여 유도된 HQSAR 모델은 매우 양호한 예측성(cross-validated $r^2_{cv.},\;q^2=0.674)$과 적합성(non-cross-validated, $r^2_{ncv}=0.936)$을 나타내었다. 멜라닌생성 저해활성과 가수분해 반응성은 공히, (A)가 (B)보다 컸으며(A$R_l$-치환기가 $R_2$-치환기보다 저해활성에 의존적인 경향을 나타내었다$(R_l>R_2)$. 또한, 경계분자궤도(FMO) 이론에 따라 가수분해 반응은 (A), (B)의 LUMO와 물분자의 HOMO 사이에 강한 상호작용으로 orbital-control 반응인 친핵성 첨가-제거반응$(Ad_{N-E})$이 주로 일어나는 것을 알 수 있었다.

• 약학회지
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• 제47권3호
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• pp.130-134
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• 2003

For the development of new synthetic method for unnatural amino acid esters, N-aryl phenylglycine Ο-alkyl esters 4a∼i were synthesized through base-catalyzed hydrolysis of 1,5-diphenylhydantoins 1a∼b and Ο-alkylation in 16∼87％ yield. An efficient and practical route for final 4a∼i was that the starting materials 1a∼b were heated in dil-methanol for 30 minute using sodium hydroxide or potassium hydroxide and evaporated. In addition, reaction mixture were refluxed for 1 h in DMF. All synthetic process from hydantoin to N-aryl phenylglycine Ο-alkyl esters 4a∼i could be carried out in one-pot without isolation of intermediates.