Efficient Regio- and Stereoselective
Synthesis of 5-Alkyl(aryl)idene- and 5-[Iodoalkyl(aryl)idene]-1H-pyrrol-2(5H)-ones
via Electrophilic Cyclization

Khalil Cherry; Alain Duchêne; Jérôme Thibonnet; Jean-Luc Parrain; Elsa Anselmi; Mohamed Abarbri

doi:10.1055/s-0028-1083257

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Synthesis 2009(2): 257-270
DOI: 10.1055/s-0028-1083257

PAPER

Efficient Regio- and Stereoselective Synthesis of 5-Alkyl(aryl)idene- and 5-[Iodoalkyl(aryl)idene]-1H-pyrrol-2(5H)-ones via Electrophilic Cyclization

Khalil Cherry^a, Alain Duchêne^a, Jérôme Thibonnet^a, Jean-Luc Parrain^b, Elsa Anselmi^a, Mohamed Abarbri*^a
^a Laboratoire de Physicochimie des Matériaux et de Biomolécules, EA 4244, Faculté des Sciences de Tours, Parc de Grandmont, Université de Tours, 37200 Tours, France
Fax: +33(2)47367073; e-Mail: mohamed.abarbri@univ-tours.fr;
^b Institut des Sciences Moléculaires de Marseille, équipe Stéréo UMR-CNRS 6263, Université Paul Cézanne, Campus Scientifique de Saint Jérôme, Avenue Escadrille Normandie-Niemen, Service 532, 13397 Marseille cedex 20, France

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Publikationsverlauf

Received 29 July 2008
Publikationsdatum:
01. Dezember 2008 (online)

Abstract
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Abstract

A variety of substituted 5-alkyl(aryl)idene- and 5-[iodoalkyl(aryl)idene]-1H-pyrrol-2(5H)-ones were readily prepared with good yields under very mild reaction conditions by the iodocyclization of (2Z,4E)-dienamides and (Z)-alk-2-en-4-ynamides with iodine monochloride. 3-Ylidene-isoindolin-1-ones were also synthesized in moderate to good yields under the same conditions. The methodology proceeded with total regioselectivity in all cases and was applied to the synthesis of new unsaturated lactam compounds.

Key words

alkylidene-pyrrolones - electrophilic cyclization - dienamides - regioselectivity - iodocyclization

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