Peculiar reaction behavior of 1,3-oxathiolan-5-one toward various reagents: Molecular modeling studies and in vitro antioxidant and cytotoxicity evaluation

Chemical reactivity of 2-methyl-2-phenyl-1,3-oxathiolan-5-one (<b>1</b>) toward various reagents such as hydroxyaldehyde, ketone, α,β unsaturated carbonyl compounds, heterocyclic amine, hydrazine, and hydrazide to give unpredicative opened and fused heterocyclic systems was investigated. Moreover, treatment of compound <b>1</b> with bromoester to afford the respective fused system, 2-methyl-2-phenylfuro[3,2-d][1,3]oxathiol-5(6<i>H</i>)-one (<b>6</b>) was implemented. Besides, ¹H–¹H nuclear overhauser effect spectroscopy was used for full confirmation of the compound <b>19</b>. In addition, the density functional theory modeling study outcomes were discussed and all of the new synthesized compounds were evaluated as antioxidants and cytotoxicity assay against hepatocellular carcinoma cell line.