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Paper | Regular issue | Vol 75, No. 2, 2008, pp.331-338
Published online, 9th November, 2007
DOI: 10.3987/COM-07-11210
First Example of Diels-Alder Reaction of 4-(1-Ethenylsubstituted)-3-methylisoxazoles with Acetylenedicarboxylates

Stefano Chimichi,* Barbara Cosimelli,* Marco Boccalini, Alessandra Matteucci, and Abdelatif Messaoudi

*Dipartimento di Chimica Organica ”U. Schiff” and Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamente Attivi (HeteroBioLab), Via della Lastruccia n. 13, I-50019 Sesto, Italy


The first example of a [4+2] cycloaddition reaction of 4-(1-ethenylsubstituted)isoxazoles with acetylenedicarboxylates is reported, while the corresponding 5-substituted isomers do not react with the same dienophile; density functional theory (DFT) calculation indicate the electronic origin of the different behaviour.