Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring

Ozer G., Saracoglu N., Balci M.

JOURNAL OF ORGANIC CHEMISTRY, vol.68, no.18, pp.7009-7015, 2003 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 68 Issue: 18
  • Publication Date: 2003
  • Doi Number: 10.1021/jo0345300
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7009-7015
  • Middle East Technical University Affiliated: No

Abstract

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.