Artigo de Periódico
Synthesis of multi-functionalized 1-azabicycles through MAOS acid catalyzed formal aza-[3+3] cycloaddition of heterocyclic enaminones with oxazolones
Fecha
2013Registro en:
0040-4039
v. 54, n. 26
Autor
Cunha, Silvio do Desterro
Santos Filho, Raimundo Francisco dos
Saraiva, Katharine Hodel
Santos, Alene Vanessa Azevedo dos
Menezes, Diego
Cunha, Silvio do Desterro
Santos Filho, Raimundo Francisco dos
Saraiva, Katharine Hodel
Santos, Alene Vanessa Azevedo dos
Menezes, Diego
Institución
Resumen
This study describes the combination of microwave heating and green acid catalysis by Bi(NO3)3·5H2O and AcOH as a practical one-pot diastereoselective synthetic route to alkaloid-like multi-functionalized 3,4-disubstituted indolizidinones and quinolizidinones from cyclic enaminones and Erlenmeyer–Plöchl azalactone derivatives, as an alternative methodology to access these synthetically and biologically important classes of structural scaffolds in a simple way. The potential biological activity of some synthesized alkaloid-like derivatives was tested against the human tumor lineage hepatoma (HepG-2), and their inhibitory effect evaluated after 24 and 48 h. The indolizidine-like scaffold appears to be crucial to biological activity in the investigated compounds.