Synlett 2010(9): 1363-1366  
DOI: 10.1055/s-0029-1219834
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Unusual [4+2]-Cycloaddition Reaction between Electron-Poor 1,2-Diaza-1,3-dienes and Electron-Poor Alkenes: Useful Entry to Novel Tetrahydropyridazines

Maurizio D’Auria*a, Rocco Racioppia, Orazio A. Attanasib, Fabio Mantellinib
a Dipartimento di Chimica, Università della Basilicata, Via N. Sauro 85, 85100 Potenza, Italy
Fax: +39(0971)202223; e-Mail: maurizio.dauria@unibas.it;
b Istituto di Chimica Organica della Facoltà di Scienze e Tecnologie, Università degli Studi di Urbino ‘Carlo Bo’, Via I. Maggetti 24, 61029 Urbino, Italy
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Publikationsverlauf

Received 26 February 2010
Publikationsdatum:
15. April 2010 (online)

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Abstract

1,2-Diaza-1,3-dienes react with electron-poor alkenes to give the corresponding tetrahydropyridazines with high regio- and stereoselectivity. Both regio- and stereoselectivity can be explained considering the interaction between the LUMO of the 1,2-diaza-1,3-diene and HOMO-1 of the alkene.