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

• Дата: 2020
• Автори: Riabchenko, Anastasiia A., Shablykina, Olga V., Shilin, Serhiy V., Chumachenko, Svitlana A., Khilya, Volodymyr P.
• Формат: Стаття
• Мова: English
• Опубліковано: V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2020
• Теми: sulfonamides; amino acids; 3-phenylisocoumarin; sulfochlorination; сульфонаміди; амінокислоти; 3-фенілізокумарин; сульфохлорування
• Онлайн доступ: 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