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

Britto, Sebastian; Renaud, Philippe; Nallu, Maruthai (2014). Synthesis, spectral, and anti-microbial studies of thioiminium iodides and amine hydrochlorides. Spectrochimica acta. Part A - molecular and biomolecular spectroscopy, 120, pp. 489-493. Elsevier 10.1016/j.saa.2013.09.108

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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.

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