Synthesis of the possible carcinogenic dihydrodiol and diol epoxide of phthalazine

Date

2005-02-07

Author

Ozer, G
Saracoglu, N
Menzek, A
Balcı, Metin

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Inverse-Diels-Alder reaction of dimethyl 1,2,4,5 -tetrazine-3,6-dicarboxylate with benzene cis-diol gave dihydrodiol coninini 2 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 dihydropyfidazine 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.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/51579

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2004.11.071

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

G. Ozer, N. Saracoglu, A. Menzek, and M. Balcı, “Synthesis of the possible carcinogenic dihydrodiol and diol epoxide of phthalazine,” TETRAHEDRON, pp. 1545–1550, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51579.