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Diels–Alder reactions of pyridinone o-quinodimethanes generated from substituted sulfolene[3,4-c]pyridin-4(1H)-ones

✍ Scribed by Tom C Govaerts; Ilse A Vogels; Frans Compernolle; Georges J Hoornaert

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 459 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00826-3

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✦ Synopsis

1-Benzyl-3-(bromomethyl)-2(1H)-pyrazinone was converted to [3,4-c] sulfolene pyridinone 8a and further (1-or 3-) substituted derivatives having a dienophilic side chain on the sulfolene ring. Thermolytic extrusion of sulfur dioxide from o-QDM precursor 8 led to generation of 3,4-dimethylene-2(1H)-pyrazinone 9, which was reacted in situ with various dienophiles. Thermolysis of the substituted precursors resulted in intramolecular cycloaddition of the corresponding o-QDM intermediates

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