Belveren, Samet, Larrañaga Agirre, Olatz, Poyraz, Samet, Dondas, H. Ali, Ülger, Mahmut, Şahin, Ertan, Ferrándiz-Saperas, Marcos, Sansano, Jose M., Retamosa, Maria de Gracia, Cózar Ruano, Abel de
From Bioactive Pyrrolidino[3,4-c]pyrrolidines to more Bioactive Pyrrolidino[3,4-b]pyrrolidines via Ring-Opening/Ring-Closing Promoted by Sodium Methoxide
Synthesis. 2019, 51(07): 1565-1577. doi:10.1055/s-0037-1611356
URI: http://hdl.handle.net/10045/89887
DOI: 10.1055/s-0037-1611356
ISSN: 0039-7881 (Print)
Abstract: 
The process involving a rearrangement of pyrrolidino[3,4-c]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.
Keywords:Cycloaddition, Azomethine ylides, Rearrangement, Antibacterials, DFT calculations
Georg Thieme Verlag
info:eu-repo/semantics/article