Synlett 2008(17): 2613-2616  
DOI: 10.1055/s-0028-1083515
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Ethyl Vinyl Ether as a Synthetic Equivalent of Acetylene in a DABCO-Catalyzed Microwave-Assisted Diels-Alder-Elimination Reaction Sequence Starting from 2H-Pyran-2-ones

Krištof Kranjc*, Marijan Kočevar
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
Fax: +386(1)2419220; e-Mail: kristof.kranjc@fkkt.uni-lj.si;
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Publication History

Received 23 June 2008
Publication Date:
01 October 2008 (online)

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Abstract

We present a study of the Diels-Alder reaction between various electron-deficient 2H-pyran-2-ones and ethyl vinyl ether. This microwave-accelerated sequence of a cycloaddition followed by a retro-Diels-Alder reaction (the elimination of CO2) and a second elimination step of EtOH yields substituted aniline derivatives. The reaction sequence is greatly accelerated by the application of DABCO as a suitable base.