Synthesis of Bis(indolyl)methanes via thiourea organocatalysts carrying 3,5-bis(trifluoromethyl)phenyl or 3,5-dichlorophenyl moieties

Bis(indolyl)methane derivatives (BIMs) were synthesized in moderate to good yields by electrophilic aromatic substitution of indole ( 27 ) with various aldehydes or imines in the presence of thiourea organocatalysts carrying 3,5-bis(trifluoromethyl)phenyl or 3,5-dichlorophenyl moieties. Reactions were performed under conventional and microwave (MW) irradiation without solvent. The most active organocatalyst for aldehydes was thiourea 3 and for imines, the thiourea 6 . For compound 11 derived from 2,4,6trimethoxybenzaldehyde ( 30 ) its structure was confirmed by X-ray analysis. Furthermore, some of the synthesized compounds were evaluated for their effectiveness as antibacterials. Compounds 3, 9, 10 and 13 showed inhibitory activity against Gram positive bacteria whereas compound 5 showed inhibitory activity against Gram positive and Gram negative bacteria.

Automated summary

Bis(indolyl)methane derivatives were synthesized using an organic catalyst, and their antibacterial activity was evaluated.