Synthesis of the possible carcinogenic dihydrodiol and diol epoxide of phthalazine

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• 作者：Ö ; zer ; Galip ; Saracoglu ; Nurullah ; Menzek ; Abdullah ; Balci ; Metin
• 关键词：Phthalazine ; Dihydrodiol ; Epoxydiol ; Tetrazine ; Cycloaddition ; Photooxygenation
• 刊名：Tetrahedron
• 出版年：2005
• 出版时间：February 7, 2005
• 年：2005
• 卷：61
• 期：6
• 页码：1545-1550
• 全文大小：216 K

文摘

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.