From Bioactive Pyrrolidino[3,4-c] pyrrolidines to more Bioactive Pyrrolidino[3,4-b] pyrrolidines via Ring-Opening/ Ring-Closing Promoted by Sodium Methoxide

Belveren S., LARRAÑAGA O., Poyraz S., Dondas H. A., Ulger M., ŞAHİN E., ...Daha Fazla

SYNTHESIS-STUTTGART, cilt.51, sa.7, ss.1565-1577, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 51 Sayı: 7
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1055/s-0037-1611356
  • Dergi Adı: SYNTHESIS-STUTTGART
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1565-1577
  • Anahtar Kelimeler: cycloaddition, azomethine ylides, rearrangement, antibacterials, DFT calculations, DERIVATIVES, INDOLE, CYCLOADDITIONS, ANTIBACTERIAL, AGENTS
  • Atatürk Üniversitesi Adresli: Evet

Özet

The process involving a rearrangement of pyrrolidino[ 3,4c] pyrrolidine to another pyrrolidino[ 3,4-b] pyrrolidine using sodium methoxide as base is fully studied. The effects of the substituents are analyzed during the ring-opening/ ring-closing sequence. Computational studies are also performed to explain the importance of susbstituents and quaternary carbons, especially when the (3-indolyl) methyl is present in the starting material. Finally, all the samples are evaluated as potential candidates for antibacterial and antimycobacterial activities.