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Synthesis 1995; 1995(3): 236-238
DOI: 10.1055/s-1995-3898
short paper
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Diethyl 2-Oxopent-3-ynedioate: Synthesis and First Cyclizations of a Novel, Reactive Alkyne

Torsten Blitzke, Dieter Sicker* , Horst Wilde
  • *Institut für Organische Chemie, Universität Leipzig, Talstr. 35, D-04103 Leipzig, Germany, Fax +49(341)281900
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Publication Date:
31 December 2000 (online)

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Diethyl 2-oxopent-3-ynedioate (3), the carbonyl homologue of diethyl acetylenedicarboxylate, is prepared by thermolysis of bis(ethoxalyl)methylenetriphenylphosphorane (2) and is found to be a reactive building block. Diels-Alder reaction of its alkyne unit with 1,3-diphenylisobenzofuran affords the cycloadduct 4, whereas reaction with binucleophiles such as ortho-XH-anilines (X = O,NH,S) leads to the incorporation of the oxoalkyne C3-segment into the heterocycles 5-7.

β, γ, β’, γ’-tetraoxophosphorus ylide - 2-oxoalkyne - diethyl 2-oxopent-3-ynedioate - Diels-Alder reaction - cyclocondensation