Synthesis of the possible carcinogenic dihydrodiol and diol epoxide of phthalazine |
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Authors: | Galip Özer Abdullah Menzek |
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Institution: | a Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey b Department of Chemistry, Middle East Technical University, Inonu Bulvari, 06531 Ankara, Turkey |
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Abstract: | Inverse-Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with benzene cis-diol gave dihydrodiol containing the 1,4-dihydropyridazine ring. Attempts at oxidation of the dihydropyridazine ring with PIFA and MnO2 resulted in the formation of 5- and 5,6-dihydroxy-phthalazine derivatives. The oxidation of the dihydropyridazine ring was achieved by way of photooxygenation. The phthalazine type dihydrodiol is unstable and easily undergoes aromatization. The Diels-Alder reaction of tetrazine with cyclohexadiene acetonide and epoxy-ketal cyclohexene as a dienophile was investigated. These reactions led to the possible carcinogenic phthalazine type of dihydrodiol and diol epoxide where the hydroxyl groups are protected. |
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Keywords: | Phthalazine Dihydrodiol Epoxydiol Tetrazine Cycloaddition Photooxygenation |
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