Одержання амінокислотних сульфонамідів на основі 4-(1-оксо-1Н-ізохромен-3-іл)бензенсульфонілхлориду

• Datum: 2020
• Автори та афіліації: Anastasiia A. Riabchenko — Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine; Olga V. Shablykina — Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine; V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine; Serhiy V. Shilin — Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine; Svitlana A. Chumachenko — V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, 1 Murmanska St., Kyiv, 02094, Ukraine; Volodymyr P. Khilya — Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine
• Ключові слова: keywords
• Hauptverfasser: Riabchenko, Anastasiia A., Shablykina, Olga V., Shilin, Serhiy V., Chumachenko, Svitlana A., Khilya, Volodymyr P.
• Format: Artikel
• Sprache: Englisch
• Veröffentlicht: V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2020
• Schlagworte: сульфонаміди; амінокислоти; 3-фенілізокумарин; сульфохлорування
• Online Zugang: https://bioorganica.com.ua/index.php/journal/article/view/38
• Назва журналу: Ukrainica Bioorganica Acta

The creation of new amino acid derivatives of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride 1 was investigated. The interaction of the sulfonyl chloride 1 with amino acid methyl esters (hydrochlorides) in 1,4-dioxane in the presence of triethylamine led to the corresponding amino acid sulfonamide derivatives of isocoumarin. The reaction of the sulfonyl chloride 1 with phenylalanine in the basic aqueous solution was complicated by the lactone system disclosure and led to 2'-carboxydeoxybenzoin ultimately (namely, 2-(2-(4-(N-(1-carboxy-2-phenylethyl)sulfamoyl)phenyl)-2-oxoethyl)benzoic acid). Similar product was obtained by the alkali hydrolysis of methyl ((4-(1-oxo-1H-isochromen-3-yl)phenyl)sulfonyl)leucinate