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

被引：13

作者：

Cherry, Khalil ^{[1
]}

Duchene, Alain ^{[1
]}

Thibonnet, Jerome ^{[1
]}

Parrain, Jean-Luc ^{[2
]}

Anselmi, Elsa ^{[1
]}

Abarbri, Mohamed ^{[1
]}

机构：

[1] Univ Tours, Fac Sci Tours, Lab Physicochim Mat & Biomol, EA 4244, F-37200 Tours, France

[2] Univ Paul Cezanne, CNRS, UMR 6263, Equipe Stereo,Inst Sci Mol Marseille,Serv 532, F-13397 Marseille 20, France

来源：

SYNTHESIS-STUTTGART | 2009年 / 02期

关键词：

alkylidene-pyrrolones; electrophilic cyclization; dienamides; regioselectivity; iodocyclization; MULTIPLY-SUBSTITUTED IMINOCYCLOPENTADIENES; CROSS-COUPLING REACTIONS; ONE-POT; 3-COMPONENT; SELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; GAMMA-ALKYLIDENEBUTENOLIDES; STEREOCONTROLLED SYNTHESIS; CATALYZED LACTONIZATION; ORGANOMETALLIC REAGENTS; 3-IODOBUT-3-ENOIC ACID;

D O I：

10.1055/s-0028-1083257

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：257 / 270

页数：14

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