alpha-Amination and the 5-exo-trig cyclization reaction of sulfur-containing Schiff bases with N-phenyltriazolinedione and their anti-lipid peroxidation activity

Abstract

Triazolinedione quenches efficiently the 1,2-dipoles from Schiff bases of glycine esters which are formed via a [1,2-H]-prototropic shift of their alpha-hydrogens, and affords the respective alpha-aminated products in good yields. Competition experiments show a stabilization of the 1,2-dipole from the sulfide substituent. 5-exo-trig cyclization of N-PhTAD with Schiff bases of other amino acids gave triazolines. The antioxidative and lipoxygenase inhibitory activities of the novel synthesized compounds were studied. (C) 2016 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.