The reactions of dimethyl 2,5-bis(diazo)-3,4-dikentoadipate with aromatic and heteroaromatic compounds |
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Authors: | CW Bird CK Wong DY Wong FLK Koh |
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Institution: | Department of Chemistry, Queen Elizabeth College, Campden Hill, London W8 7AH U.K. |
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Abstract: | Heating the title compound with benzene provides a mixture of dimethyl 1,3-dihydroxynaphthalene-2,4-dicarboxylate and 3-carbomethoxy-4-hydroxy-5-phenylpyrone which rearranges on melting to the aforementioned naphthalene derivative. The initial substitution reaction appears to proceed through an intermediary pyronyl cation. The scope of this potential ring annelation reaction has been investigated for a range of aromatic and heteroaromatic compounds. Heating with basic substrates converts the bisdazo compound into dimethyl 4-hydroxypyrazole-3,5-dicarboxylate, while heating with isopropanol yields dimethyl 4,5-dihydroxypyridazine-3,6-dicarboxylate. |
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