• Bulletin of the Korean Chemical Society
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• v.25 no.5
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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.

• Journal of the Korean Chemical Society
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• v.48 no.4
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• pp.385-393
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• 2004

2-Ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8) was synthesized from benzofuroxan and ethyl acetoacetate. The reaction of compound 8 with hydrazine hydrate or selenium dioxide gave 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide (9) or 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10), respectively. The reaction of compound 9 with alkanoyl chlorides, benzoyl chlorides, heteroacyl chlorides, and benzenesulfonyl chlorides afforded 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 1,4-dioxides (11-14), respectively. The reaction of compound 9 with sodium azide gave 2-azidocarbonyl-3-methylquinoxaline 1,4-dioxide (15), and then its refluxing in dioxane/alcohols resulted in the Curtius rearrangement to give N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamates (16). The reaction of compound 15 with substituted anilines afforded 2-(3-substituted phenylureido)-3-methylquinoxaline 1,4-dioxides (17). The reaction of compound 10 with benzoic hydrazide or substituted anilines provided quinoxaline 1,4-di-oxides (18, 19), respectively. The herbicidal and fungicidal activities of the synthesized compounds were investigated.

• Journal of the Korean Chemical Society
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• v.17 no.2
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• pp.136-141
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• 1973

DL-1-aminobutylphosphonic acid was synthesized from the pentanoic acid which was prepared from the butyl alcohol, by the modified Curtius reaction. DL-2-amino-2-carboxyethylphosphonic acid was also synthesized from the pyruvic acid was also synthesized from the pyruvic acid. Four previously unreported N-acylated derivatives were prepared according to the modified Schotten-Baumann method. They are as follows; 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. The products were identified by the methods of elemental analysis, infrared spectra, ninhydrin test and neutralization equivalent.

• Journal of the Korean Chemical Society
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• v.15 no.1
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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.

• Journal of the Korean Chemical Society
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• v.15 no.5
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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.