Journal of the Brazilian Chemical Society
On-line version ISSN 1678-4790
CUNHA, Silvio et al. The Michael Reaction of Enaminones with N-(p-tolyl)-maleimide: Synthesis and Structural Analysis of Succinimide-enaminones. J. Braz. Chem. Soc. [online]. 2002, vol.13, n.5, pp. 629-634. ISSN 1678-4790. http://dx.doi.org/10.1590/S0103-50532002000500014.
The reaction of N-(p-tolyl)-maleimide with enaminones afforded succinimide-containing enaminones in moderate to good yields, and these compounds were evaluated against E. coli and S. aureus, but no significant antibacterial activity was observed. The regiochemistry of the compounds was examined mechanistically within frontier molecular orbital considerations. In the solid state three-dimensional structure there is the formation of cooperative inter- and intramolecular NH...O and CH...O hydrogen bonding.
Keywords : enaminones; succinimide; maleimide.