Reaction of 5-alkyl- and 5-arylfuran-2(3H)-ones with aliphatic amino acids

Abstract

Amino acids are polyfunctional reagents allowing target-oriented synthesis of various heterocyclic structures. The reaction of cysteine with levulinic acid gives a dibasic acid which readily loses water at elevated temperature, yielding bicyclothiazinone [1]. In the reaction of cysteine with 5-methylfuran-2(3H)-one, the amino acid initially adds to the double bond in the furan ring, and opening of the latter and subsequent dehydration lead to heterocyclic compound. The product is stabilized via further dehydration with formation of 5-oxothiazolidinecarboxylic acid [2]. The reaction of furan-2(3H)-one with L-cysteine involves initial attack by the amino group on the carbonyl carbon atom to produce oxo acid amide which is converted in solution into bicyclic hexahydropyrrolothiazole structure [3, 4]. Levulinic and β-benzoylpropionic acids were reported to react with anthranilic acid on heating in dichlorobenzene to produce 3a-methyland 3a-phenyl3,3a-dihydro-5H-benzo[d]pyrrolo[1,2-b][1,3]oxazine1,5(2H)-diones, respectively [5, 6]. In the reactions of anthranilic acid amide with levulinic and β-benzoylpropionic acids on heating in chlorobenzene 3a-methyland 3a-phenyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,6-diones were obtained, respectively. Binucleophilic α-amino acids (cysteine, penicillamine, serine, and threonine) were studied in reactions