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Abstract Reaction of phthalyl glycyl with tryptophan yielded compound which cyclized in acetic anhydride to give 2-[4-(1H-Indol-3-ylmethyl)-5-oxooxazolidin- 2-ylmethyl]-isoindole-1,3-dione (1) via Erlenmeyer synthesis. The reactivity of oxazolone derivative towards nitrogen nucleophiles was investigated. It was found that the oxazolone (1) reacted with primary amines in DMF solution and yielded the corresponding 2-[2-(1,3-Dioxo-1,3- dihydro-isoindol-2-yl)- acetylami-no] -3-(1H-indol-3-yl)-aryl-propionamide (2a-f). It also reacts with secondary amine namely piperidine to yield 2-(1, 3-Dioxo-1, 3-dihydro-isoindol-2-yl)-N-[1-(1H-indol-3-ylmethyl)-2-oxo- 2-piperidin-1-yl-ethyl]-acetamide (3). Compound (1) also reacted with amino acids in DMF solution to give the corresponding [2-[2-(2,3-Dioxo-1,3-dihydro-isoindol-2-yl)- acetylamino]-3-(1H-indol-3-yl)-propiony-lamino]-(acetic/prop-ionic/-3- (1H-indol-3-yl)-propionic) acid (4a-c). The reaction of (1) with hydrazine hydrate in DMF solution afforded 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-N-[2-(1H-indol-3-yl)-1-(N’- phenyl-hydrazinocarbonyl)-ethyl]-acetamide (5).similary, it condensed with phenyl hydrazine in DMF solution and afforded 2-(1,3-Dioxo-1,3- dihydro-isoindol-2-yl)-N-[2-(1H-indol-3-yl)-1-(N’-phenylhydrazinocarbonyl)- ethyl]-acetamide |