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

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Belveren S., Larranaga O., Poyraz S., Dondas H. A., Ulger M., ŞAHİN E., ...More

SYNTHESIS-STUTTGART, vol.51, no.7, pp.1565-1577, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 51 Issue: 7
  • Publication Date: 2019
  • Doi Number: 10.1055/s-0037-1611356
  • Journal Name: SYNTHESIS-STUTTGART
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1565-1577
  • Keywords: cycloaddition, azomethine ylides, rearrangement, antibacterials, DFT calculations, DERIVATIVES, INDOLE, CYCLOADDITIONS, ANTIBACTERIAL, AGENTS
  • Çukurova University Affiliated: No

Abstract

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.