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Synthesis 1996; 1996(4): 519-524
DOI: 10.1055/s-1996-4236
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Synthesis and Reactivity of (3-Oxo-2,3-dihydro-1H-ylidene)acetic Acid Alkyl Esters in Diels-Alder Reactions

Jean-Yves Mérour* , Lucien Chichereau, Eric Desarbre, Philippe Gadonneix
  • *Institut de Chimie Organique et Analytique, URA CNRS, BP 6759, Université d’Orléans, F-45067 Orléans Cedex 02, France, Fax +33(38)417078
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Publication Date:
31 December 2000 (online)

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Aldolization reactions of 1-acetyl-1H-indol-3(2H)-one with glyoxal derivatives afforded (1-acetyl-3-oxo-2,3-dihydro-1H-indol-2-ylidene)acetic acid ester derivatives 2 and 3. Spiro compounds 6 were obtained by Diels-Alder reactions of 2; inverse electron demand Diels-Alder reactions of 2 afforded pyrano indoles 8.

glyoxal derivatives - aldolisation - 1H-indol-3(2H)-one - pyrrolo[2,3-b]pyridin-3-one - Diels-Alder reactions