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  • Chem Sci Trans., 2013, 2(2),  pp 649-655  

    DOI:10.7598/cst2013.377

    Research Article

    Synthesis and Characterization of Substituted Phenyl Azetidines as Potential Antimicrobial Agents

  • K. DORASWAMY and P. VENKATA RAMANA
  • Department of Chemistry, Sri Krishnadevaraya University, Anantapur- 515 003, India
  • Abstract

    The reaction of 2-(4-bromo phenyl) methyl cyanide (1a) with ethylchloroformate in the presence of n-butyl lithium gave ethyl-2-(4-bromo phenyl)-2-cyano acetate (2a). 2a on reduction with sodium borohydride yields 3-amino-2-(4-bromo phenyl) propan-1-ol (3a). Compound 3a on further reaction with tert butyloxy anhydride in presence of triethylamine afford tert-butyl-2-(4-bromo phenyl)-3-hydroxy propyl carbamate (4a). 4a on treatment with tosyl chloride gave 2-(4-bromo phenyl)-3-(tertiarybutyloxy carbonyl amino)-propan-1-ol-(4-toluene sulphonate) (5a). Compound 5a on cyclization followed by hydrolysis gave 3-(4-bromo phenyl) azetidine (7a). Compounds 2b-2e, 3b-3e, 4b-4e, 5b-5e, 6b-6e and 7b-e were synthesized by a similar method. The compounds are characterized by elemental analysis, IR, 1H NMR and Mass spectral analysis and screened for antimicrobial activity.

    Keywords

    Substituted azetidines, Borane reduction, Antimicrobial activity

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