Chemistry of bicyclic endoperoxides derived from dihydropyridine derivatives: Attempted synthesis of polyhydroxypiperidine derivatives

Salamci E., BAYRAM B., BALCI M.

TURKISH JOURNAL OF CHEMISTRY, cilt.30, sa.4, ss.441-449, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 30 Sayı: 4
  • Basım Tarihi: 2006
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.441-449
  • Atatürk Üniversitesi Adresli: Evet

Özet

To achieve the synthesis of azasugar derivatives with the utilization of singlet oxygen, pyridine was used as the starting material. The reduction of pyridine followed by a singlet oxygen reaction afforded cyclic aza-endoperoxides (14 and 16). However, many attempts were made to convert the azaendoperoxides to the corresponding di- and triacetates without success. However, the base-catalyzed rearrangement of 14 gave unprecedented rearrangement products 23 and 24.