Abstract
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.
Highlights
Synthetic [1,2] and natural [2,3] сompounds that contain the isocoumarin (1H-isochromen-1-one) fragment are well known group of oxygen containing heterocycle
Isocoumarins can be found in the scientific literature not as often as isomeric chromones and coumarins
It can be explained by the fact that the existing methods for synthesis of isocoumarins and their derivatives [1, 7] do not allow obtaining structures with certain functional groups
Summary
Synthetic [1,2] and natural [2,3] сompounds that contain the isocoumarin (1H-isochromen-1-one) fragment are well known group of oxygen containing heterocycle. These substances have a tremendous potential as starting materials in synthetic organic chemistry (synthesis of isoquinolines [4]) or as bioactive compounds [5,6]. The electrophilic substitution reactions for isocoumarin compounds have not been widely explored as a possible route for their chemical modification. It can be viewed as an opportunity to tackle the problem. It can be viewed as an opportunity to tackle the problem. [10,11,12]
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