Abstract
AbstractMetalation of 1‐methylpyrrole using n‐butyllithium and tetramethylethylenediamine (TMEDA) in ether furnished 1‐methyl‐2‐pyrrolyllithium, which in turn was converted to 1‐methyl‐2‐methylthiopyrrole upon treatment with dimethyldisulfide. Further formylation with dimethylformamide, phosphorus oxychloride in dichloroethane led to the corresponding pyrrole‐2‐carboxaldehyde, which was then condensed with malononitrile and methylcyanoacetate under Knoevenagel reaction conditions to give 2‐cyano‐3‐(1‐methyl‐5‐methylthio‐2‐pyrrolyl)acrylonitrile and 2‐cyano‐3‐(1‐methyl‐5‐methylthio‐2‐pyrrolyl)acrylic acid methyl ester, respectively. Their oxidation by hydrogen peroxide furnished the corresponding sulfones. Analogously, 5‐phenylthio derivatives were prepared.
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