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Gold(I)-Catalyzed Cyclization of β-Allenylhydrazones: An Efficient Synthesis of Multisubstituted N-Aminopyrroles

Erica Benedetti, Gilles Lemière, Laure-Lise Chapellet, Andrea Penoni, Giovanni Palmisano, Max Malacria*, Jean-Philippe Goddard* and Louis Fensterbank*

*Institut Parisien de Chimie Molculaire (UMR CNRS 7201), FR 2769 UPMC-Paris 06, C. 229, 4 Place Jussieu, 75005, Paris, France, Email: louis.fensterbankupmc.fr, jean-philippe.goddardupmc.fr, max.malacriaupmc.fr

E. Benedetti, G. Lemière, L.-L. Chapellet, A. Penoni, G. Palmisano, M. Malacria, J.-P. Goddard, L. Fensterband, Org. Lett., 2010, 12, 4396-4399.

DOI: 10.1021/ol101889h (free Supporting Information)



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Abstract

A mild, gold(I)-catalyzed cycloisomerization of β-allenylhydrazones provides an efficient access to multisubstituted N-aminopyrroles in good to excellent yields with short reaction times through a selective intramolecular 1,2-alkyl or -aryl migration. This intramolecular cyclization can be applied either to alkyl- or aryl-substituted allenes.

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Key Words

Pyrroles, Microwave Synthesis


ID: J54-Y2010-2780