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Synthesis 1990; 1990(11): 1005-1007
DOI: 10.1055/s-1990-27077
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Reactions of Heterocyclic Quinone Methides: 1-Methyl-3-methylene-2,4(1H,3H)-quinolinedione

M. A. Chauncey* , M. F. Grundon
  • *Department of Chemistry, University of Ulster, Coleraine, Northern Ireland
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Publication Date:
17 September 2002 (online)

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1-Methyl-3-methylene-2,4(1H,3H)-quinolinedione (2), prepared from 4-hydroxy-1,3-dimethyl-2 (1H)-quinolinone (1) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) gives the dimer 3. Compound 2 also reacts in situ with 2,2-dimethyl-2H-1-benzopyran and with isopropenyl acetate to give Diels-Alder cycloaddition products.