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

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发表日期：

2024年1月1日

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Zh. S. Arustamyan,
R. E. Margaryan,
G. G. Mkryan,
A. A. Aghekyan,
H. A. Panosyan,
Zh. M. Buniatyan,
R. E. Muradyan

摘要

Abstract

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.