title: Synthesis, spectral, and anti-microbial studies of thioiminium iodides and amine hydrochlorides.
abstract: 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.
authors.affiliation: Department of Chemistry, St. Joseph's College, Tiruchirappalli 620002, India. Electronic address: brittoseba@yahoo.co.in.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Britto
authors.affiliation: Universität Bern, Departement für Chemie und Biochemie, Freiestrasse 3, 3012 Bern, Switzerland.
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud
authors.affiliation: School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, India
authors.forename: Maruthai
authors.initials: M
authors.lastname: Nallu
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D002712:Chlorides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D006801:Humans; D007454:Iodides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009181:Mycoses / Q000188:drug therapy; D013055:Spectrophotometry, Infrared
chemical_list: D000588:Amines; D000890:Anti-Infective Agents; D002712:Chlorides; D007454:Iodides
keywords: Antimicrobial screening; Bisaddition; Deprotonation; Electrophile; Nucleophile; Transmetalation