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SYNTHESIS OF 1,3- AND 1,2,3-FUNCTIONALIZED PYRROLES via Ir(I)-CATALYZED VINYLATION OF ALLYL ALCOHOLS

David Alavez-Rosas, Mauricio Maldonado-Domínguez, Oscar González-Antonio, Margarita Romero-Ávila, José Méndez-Stivalet, Blas Flores-Pérez
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Abstract


An efficient method for the preparation of 1,3-disubstituted and 1,2,3-trisubstituted pyrroles was developed through a sequence involving O-vinylation of allyl alcohols followed by Claisen rearrangement and further ozonolysis, concurring in a Paal–Knorr reaction with primary amines. Hg(II) and Ir(I) catalysts and different vinylating reagents were tested. The best results were consistently obtained with the [Ir(cod)Cl]2–vinyl acetate system. The featured methodology gives access to functionalized pyrroles in overall good yields, whose chemical architecture may awake interest for assorted applications.

 


Keywords


allyl alcohols; pyrroles; Claisen rearrangement; ozonolysis

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