Sulfanyl 5H-dihydropyrroles were synthesized through diastereoselective 1,3-dipolar cycloaddition of sulfanyl-substituted azomethine ylides from glycine esters to N-phenylmaleimide under thermal or Ag-catalyzed conditions. Further manipulation with DDQ afforded novel polysubstituted pyrroles which were more potent antioxidants and lipoxygenase inhibitors than their 5H-dihydro analogues.

Available online xxxx This work is dedicated to the memory of Professor Yiannis Elemes. Keywords: Triazolinedione Amino acid Schiff base 1,2-Dipole a-Amination 5-exo-trig cyclization a b s t r a c t 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 a-hydrogens, and affords the respective a-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.

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Corrigendum to "a-Amination and 5-exo-trig cyclization reaction of sulfur-containing Schiff bases with N-phenyltriazolinedione and their anti-lipid peroxidation activity" [