Three-component carbon-carbon bond-forming reactions for the synthesis of β-amino carbonyl compounds using maleic acid-catalyzed one-pot mannich-type reaction in ethanol

Taher-Maghsoodlou, Malek; Rasul-Mousavi, Seyyed; Roygar, Ali; Lashkari, Mojtaba

doi:10.5937/kgjsci1840071t

Cited by 2 publications

(1 citation statement)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among the green methods of asymmetric Mannich syntheses, we can mention protease-catalysed direct reaction in acetonitrile [66], N,N'-dioxide metal complexes-catalysed reaction in dichloromethane [67] and synthesis of β-amino carbonyl compounds using maleic acid in ethanol [68].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

et al. 2020

View full text Add to dashboard Cite

The tri-component synthesis of novel chiral benzimidazole Mannich bases, by reaction between benzimidazole, aqueous 30% formaldehyde and an amine, the biological evaluation and DFT studies of the new compounds are reported here. The 1 H-NMR, 13 C-NMR, FTIR spectra and elemental analysis confirm the structures of the new compounds. All synthesized compounds were screened by qualitative and quantitative methods for their in vitro antibacterial activity against 4 bacterial strains. DFT studies were accomplished using GAMESS 2012 software and HOMO-LUMO analysis allowed the calculation of electronic and structural parameters of the chiral Mannich bases. The geometry of 1-methylpiperazine, the cumulated Mullikan atomic charges of the two heteroatoms and of the methyl, and the value of the global electrophilicity index (ω = 0.0527) of the M-1 molecule is correlated with its good antimicrobial activity. It was found that the presence of saturated heterocycles from the amine molecule, 1-methyl piperazine and morpholine, respectively, contributes to an increased biological activity, compared to aromatic amino analogs, diphenylamino-, 4-nitroamino-and 4-aminobenzoic acid. The planarity of the molecules, specific bond lengths and localization of HOMO-LUMO orbitals is responsible for the best biological activities of the compounds.

show abstract

Section: Introductionmentioning

confidence: 99%