Synthesis, spectral, and anti-microbial studies of thioiminium iodides and amine hydrochlorides

•The use of simple nucleophiles results in bis and mono addition.•The ultrasound sonication is used to prepare the organocerium reagents.•The arrangement of protons in the amine hydrochlorides is investigated by COSY.•The amine hydrochlorides are found to be active against some microorganisms.•The functionalities in the molecules that cause for such activity are rationalized.

To avoid the undesired deprotonation during the addition of organolithium and organomagnesium reagents to ketones, the thioiminium salts, easily prepared from lactams and amides are converted into 2,2-disubstituted and 2-monosubstituted amines by reaction with simple nucleophiles such as organocerium and organocopper reagents. The reaction of thioiminium iodides with organocerium reagents derived by transmetalation of corresponding lithium reagents with anhydrous cerium(III) chloride has been investigated. These thioiminium iodides act as good electrophiles and accept alkylceriums towards bisaddition. The newly synthesized amines have been characterized by 1H and 13C NMR, IR and mass spectra. The amines have been converted into their hydrochlorides and characterized by COSY. These hydrochlorides have been subjected to antimicrobial screening with clinically isolated microorganisms, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhi and Candida albicans. The hydrochlorides show quite good activity against these bacteria and fungus.

Graphical abstractA series of germinal bis-alkyl cyclic amines and their hydrochlorides have been prepared by simple nucleophilic addition on appropriate thioiminium iodides using organocerium reagents. The amine hydrochlorides thus prepared display considerable antimicrobial activity.Figure optionsDownload full-size imageDownload as PowerPoint slide