Synthesis and antimicrobial activity of some new 1-methyl [(N-alkyl phthalyl)-benzimidazolo]-3'-chloro-4'-substituted azetidin-2-ones

被引:0
作者
Parmar, Shipra [1 ]
Sah, Pramilla [1 ]
机构
[1] Jai Narain Vyas Univ, Dept Chem, Jodhpur 342005, Rajasthan, India
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Alkyl phthalyl benzimidazoles (IV) were synthesized by treating o-phenylene diamine with N-phthalyl substituted amino acids (III). These were subjected to Mannich reaction using formaldehyde and ammonium chloride giving the Mannich base i.e. N-alkyl phthalyl-1-amino methyl benzimidazoles (V). Reaction of V with appropriate aromatic aldehydes under anhyd conditions yielded the Schiff's bases (VI). Cyclization of VI with chloroacetyl chloride in 1,4-dioxan in presence of triethyl amine gave 1-methyl [(N-alkyl phthalyl)-benzimidazolo]3'-chloro-4'-substituted azetidin-2-onesVII. The compounds were characterized by means of mass, IR, PMR and elemental analysis. Some of the azetidinones have shown promising antimicrobial activity.
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页码:367 / 370
页数:4
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[21]   Synthesis, biological screening and molecular modeling studies of novel 3-chloro-4-substituted-1-(2-(1H-benzimidazol-2-yl)phenyl))-azetidin-2-ones [J].
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TANAKA, K ;
NAKANO, J ;
TODO, Y ;
YAMAFUJI, T ;
HATTORI, R ;
FUKUOKA, Y ;
SAIKAWA, I .
JOURNAL OF ANTIBIOTICS, 1986, 39 (01) :76-89
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