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The treatment of 4-(4-Chloro-3-methylphenyl)-4-oxobut-2-enoic acid with benzimidazole, and 2-mercapto benzimidazole afforded aza- and thia-Michael adduct as unnatural α-amino acid 1 and α-thiaacid 6 respectively. Micheal adducts 1 and 6 are used to synthesize some antioxidant heterocycles. TAN study can be confirmed, the fused heterocycles has a lower antioxidant expt that contain sulfur atom. Quantum chemical studies of 2-mercaptobezimidazole, and its amide long chain, confirmed that N-butyl-S-benzimidazol-2-ylthioglycolate at 400 ppm was more effective antioxidant heterocycles.
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