Journal
SYNTHESIS-STUTTGART
Volume -, Issue 2, Pages 257-270Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0028-1083257
Keywords
alkylidene-pyrrolones; electrophilic cyclization; dienamides; regioselectivity; iodocyclization
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Funding
- MESR
- CNRS
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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.
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