• Bulletin of the Korean Chemical Society
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• 제25권5호
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• pp.668-672
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• 2004

This paper reports the stereoselective synthesis of a novel nucleoside, 4'-methyl branched and bicyclo [3.1.0] hexane locked-nucleoside 12, using a sequential [3,3]-sigmatropic rearrangement/carbene cycloaddition reaction/Curtius reaction strategy with a high stereoselectivity.

• 대한화학회지
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• 제48권4호
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• pp.385-393
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• 2004

Benzofuroxan과 ethyl acetoacetate를 반응시켜 2-ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8)를 합성하고, 이것을 hydrazine hydrate 또는 selenium dioxide와 반응시켜 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide (9) 또는 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10)를 합성하였다. 화합물 9를 alkanoyl chloride류, benzoyl chloride류, heteroacyl chloride류 및 benzenesulfonyl chloride류와 반응시켜 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 1,4-dioxide류 (11-14)를 합성하였다. 화합물 9를 sodium nitrite와 반응시켜 2-azidocarbonyl- 3-methylquinoxaline 1,4-dioxide (15)를 합성한 다음, 이것을 디옥산/알코올류 용매하에서 환류시켜 Curtius 자리옮김반응에 의한 N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamate류 (16)를 합성하였다. 그리고 화합물 15를 치환 아닐린류와 반응시켜 2-(3-substituted phenylureido)-3-methylquinoxaline 1,4-dioxide류 (17)를 합성하였다. 한편 화합물 10을 benzoic hydrazide 또는 치환 아닐린류와 반응시켜 quinoxaline 1,4-dioxide류 (18, 19)를 각각 합성하였다. 그리고 합성한 화합물들에 대한 제초력과 살균력도 조사하였다.

• 대한화학회지
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• 제17권2호
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• pp.136-141
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• 1973

Curtius reaction을 이용하여 pentanoic acid로부터 DL-1-aminobutylphosphonic acid를 합성하였고, pyruvic acid 로부터 DL-2-carboxyethylphosphonic acid를 합성하였다. 아직 발표된 바 없는 이들의 N-acyl유도체들을 Schotten Bauman방법 등으로 합성하였다. 그 화합물들은 다음과 같다. N-acetyl-DL-1-aminobutylphosphonic acid N-benzoyl-DL-1-aminobutylphosphonic acid N-benzoyl-DL-2-amino-2-carboxyethylphosphonic acid N-p-chlorobenzoyl-DL-2-amino-2-carboxyethylphosphonic acid. 이 유도체들은 원소분석, I${\cdot}$R spectra, ninhydrin test 및 중화당량으로 확인하였다.

• 대한화학회지
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• 제15권1호
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• pp.15-22
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• 1971

DL-1-Amino-pentyl phosphonic acid, DL-1-Aminopropyl phosphonic acid were synthesized with good yield from caproic acid and butyric acid using the modified Curtius reaction and N-derivatives, N-acetyl-DL-1-amino propyl phosphonic acid, N-acetyl-DL-1-aminopentyl phosphonic acid, N-Benzoyl-DL-1-amino-propyl phosphonic acid, were also prepared by a variety of methods including the Schotten-Baumann reaction. In addition, the chemical and physical properties of the products were investigated. All the products were also identified by means of elemental analysis, Infrared spectrophotometry, Ninhydrin test, and the determination of the neuralization equivalent.

• 대한화학회지
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• 제15권5호
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• pp.275-280
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• 1971

Six previously unreported N-acylated-DL-1-amino alkyl phosphonic acids were prepared; N-Acetyl-DL-1-amino-3-methyl butyl phosphonic acidN-Benzoyl-DL-1-amino-2-methyl propyl phosphonic acidN-Benzoyl-DL-1-amino-3-methyl butyl phosphonic acidN-Benzoyl-DL-1-amino-2-methyl butyl phosphonic acidN-Acetyl-DL-1-amino-2-methyl propyl phosphonic acidN-Acetyl-DL-1-amino-2-methyl butyl phosphonic acidThe first four compounds were characterized, and the last two compounds were obtained in the crude oil state. The above three DL-1-amino-alkyl phosphonic acid were synthesized from iso-valeric acid, iso-caproic acid and ${\beta}$-methyl valeric acid using Hell-Volhard-Zelinsky reaction, the condensation reaction with triethyl-phosphite and the modified Curtius Reaction. Iso-caproic acid and ${\beta$-methyl valeric acid were prepared by the conventional methods.