The synthesis of highly functionalized pyrroles is described. The sequence involves the preliminary preparation of alpha-aminohydrazones by Michael addition of primary amines to 1,2-diaza-1,3-butadienes. The treatment of these compounds with dialkyl acetylenedicarboxylates produces alpha-(N-enamino)-hydrazones that were converted into the corresponding pyrroles by Lewis acid-catalyzed ring closure. A screening of several Lewis/Bronsted acid catalysts was also performed
Lewis acid-catalyzed synthesis of functionalized pyrroles
ATTANASI, ORAZIO ANTONIO;BERRETTA, STEFANO;DE CRESCENTINI, LUCIA;FAVI, GIANFRANCO;MANTELLINI, FABIO
2009
Abstract
The synthesis of highly functionalized pyrroles is described. The sequence involves the preliminary preparation of alpha-aminohydrazones by Michael addition of primary amines to 1,2-diaza-1,3-butadienes. The treatment of these compounds with dialkyl acetylenedicarboxylates produces alpha-(N-enamino)-hydrazones that were converted into the corresponding pyrroles by Lewis acid-catalyzed ring closure. A screening of several Lewis/Bronsted acid catalysts was also performedFile in questo prodotto:
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