Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring

Özer G., SARAÇOĞLU N., Balci M.

JOURNAL OF ORGANIC CHEMISTRY, cilt.68, sa.18, ss.7009-7015, 2003 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 68 Sayı: 18
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1021/jo0345300
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.7009-7015
  • Ankara Üniversitesi Adresli: Hayır

Özet

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.