Synthesis and Antioxidant Activity of N-{[4-(1,3-Benzodioxol-5-yl)tetrahydro-2H-pyran-4-yl]methyl}-Substituted 3-Aryloxy-2-hydroxypropanamines, 2-Aminoacetamides, and 2-(Hetarylsulfanyl)acetamides

The alkylation of 2-(1,3-benzodioxol-5-yl)acetonitrile with bis(2-chloroethyl) ether gave 4-(1,3-ben­zo­dioxol-5-yl)-tetrahydro-2H-pyran-4-carbonitrile which was reduced with lithium tetrahydroaluminate to [4-(1,3-benzodioxol-5-yl)-tetrahydro-2H-pyran-4-yl]methanamine. The latter reacted with aryloxymethyl­oxiranes to produce the corresponding 1-(aryloxy)-3-({[4-(1,3-benzodioxol-5-yl)-tetrahydro-2H-pyran-4-yl]­methyl}amino)propan-2-ols. The reaction of the same amine with chloroacetyl chloride afforded N-{[4-(1,3-ben­zodioxol-5-yl)-tetrahydro-2H-pyran-4-yl]methyl}-2-chloroacetamide which was treated with secondary amines and hetarenethiols to obtain N-{[4-(1,3-benzodioxol-5-yl)-tetrahydro-2H-pyran-4-yl]methyl}-substi­tuted 2-amino- and 2-sulfanylacetamide derivatives. The synthesized compounds were evaluated for their antioxidant activity.