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Diels-Alder reactions of pyridinone o-quinodimethanes generated from substituted sulfolene[3,4-c]pyridin-4(1H)-ones
Authors:Tom C GovaertsIlse A Vogels  Frans CompernolleGeorges J Hoornaert
Institution:Laboratorium voor Organische Synthese, Department of Chemistry, K. U. Leuven, Celestijnenlaan 200F, B3001 Leuven, Heverlee, Belgium
Abstract: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
Keywords:ortho-quinodimethane  pyridinone  Diels-Alder reaction
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