Synthesis and Antihypoxic Properties of New 1,4-Benzodioxane Derivatives Containing a Diallyl Fragment

Abstract

The reaction of 2-(1,4-benzodioxan-6-yl)acetonitrile with 2 equiv of allyl bromide in the presence of sodium hydroxide gave 2-(1,4-benzodioxan-6-yl)-2-(prop-2-en-1-yl)pent-4-enenitrile which was reduced to 2-(1,4-benzodioxan-6-yl)-2-(prop-2-en-1-yl)pent-4-en-1-amine with lithium tetrahydridoaluminate. The ob­tained amine reacted with diethyl oxalate to produce N-substituted ethyl oxamate which was converted to oxalic acid diamides by treatment with various amines (arylalkyl- and hetarylalkylamines, N-benzylpiperazine). N-Aryloxamide derivatives were synthesized by the reaction of 2-(1,4-benzodioxan-6-yl)-2-(prop-2-en-1-yl)­pent-4-en-1-amine with ethyl N-aryloxamates. The synthesized compounds were tested for antihypoxic activity.