Synthesis of Fluoro Benzothiazoles  Comprising Azetidinone Derivatives |
Various substituted4-(m-hydroxy-p-methoxy phenyl)-1-[(6'-fluoro-7'-substituted(1,3)-benzothiazol-2'-yl) amido-2-phenyl]-3-chloro azetidin–2–one containingdifferent functional groups have been synthesized by treatingfluorochloroaniline with KSCN in presence of bromine in glacial acetic acid andammonia to get 2-amino-6-fluoro- 7-chloro-(1,3)-benzothiazole, which wastreated with anthranillic acid in presence of dry pyridine to get 2-amino-N-(6-fluoro-7-chloro-(1,3)-benzothiazol-2-yl) benzamide. To the above, refluxedwith vanillin and alcohol in presence of Conc. HCl to get2-(3-hydroxy-4-methoxy benzylidene amino phenyl amido)-6-fluoro-7-chloro-(1,3)- benzothiazole or Schiff’s base. A Solution of Schiff’s base in 1, 4-dioxanewas added to well-stirred mixture of chloroacetyl chloride and triethylamine toget Azetidinone. To the above product different primary and secondary aromaticamines in presence of DMF were treated to get newly targeted compound throughreplacing at 7th position chlorine. Thelead compounds were characterized by melting point, TLC, calculated elementalanalysis, UV, IR, 1HNMR and MASS spectral studies. The compounds were testedfor anthelmintic activity against earthworms, Perituma posthuma and showed significant activity at low and highconcentration compared to standard; still further studies are requested.