Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring

Date

2003-09-05

Author

Ozer, G
Saracoglu, N
Balcı, Metin

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Inverse-Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with unsaturated bicyclic endoperoxides gave the bicyclic endoperoxides containing the pyridazine ring. The NEt3 and CoTPP (TPP = tetraphenylporphyrin) catalyzed reaction of endoperoxide 8 resulted in the formation of hydroxy ketone 11 and cis-diol 9. Cleavage of the peroxide linkage in 8 with thiourea provided cis-diol 9. Oxidation of hydroxy ketone 11 and cis-diol 9 led to the phthalazine-5,8-dione 10. Furthermore, the various transformations of the other endoperoxides 19, 20, 22, 23, and 30 resulted in the formation of pyridazine derivatives.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/57908

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo0345300

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Graduate School of Natural and Applied Sciences, Article

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Citation Formats

G. Ozer, N. Saracoglu, and M. Balcı, “Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring,” JOURNAL OF ORGANIC CHEMISTRY, pp. 7009–7015, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57908.