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Reaction Of α-amido Sulfones With Functionalized Nitrocompounds: A New Two-step Synthesis Of N-alkoxycarbonyl-2,5-disubstituted Pyrroles

Roberto Ballini, Serena Gabrielli, Alessandro Palmieri, Marino Petrini
Published 2014 · Chemistry

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Reaction of α-amido sulfones with nitro ketals promoted by KF on alumina provides the corresponding adducts which, upon treatment with p-toluenesulfonic acid, generate the corresponding N-alkoxycarbonyl-2,5-disubstituted pyrroles. The latter transformation involves a cascade process including ketal cleavage, ring closure and final aromatization by nitrous acid elimination.

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