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Approaches to the Construction of Substituted 4-Amino-1<i>H</i>-pyrrol-2(5<i>H</i>)-ones
Fully substituted 4-aminopyrrolones are easily accessed
via simple
routes starting from imines, ketones, or α-bromophenyl acetonitriles.
Imines were reacted with KCN/NH<sub>4</sub>Cl in aqueous ethanol to
produce α-arylamino benzyl cyanides. On the other hand, ketones
were transformed to the desired α-amino nitriles using a modified
Strecker reaction. Then, α-amino nitrile precursors were allowed
to react with a suitable acyl halide to produce the corresponding
amides. Further treatment of these amides with ethanolic KOH converted
them to highly substituted 4-amino-1<i>H</i>-pyrrol-2Â(5<i>H</i>)-one derivatives in moderate to excellent yields