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Synthesis, characterization and antibacterial activity of 1‐([6‐bromo‐2‐hydroxy‐naphthalen‐1‐yl]arylphenyl)methyl)‐3‐chloro‐4‐(arylphenyl)‐azetidin‐2‐one
Author(s) -
Chopde Himani N.,
Pandhurnekar Chandrashekhar P.,
Yadao Babita G.,
Bhattacharya Doyel M.,
Mungole Arvind J.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4056
Subject(s) - chemistry , ketene , triethylamine , aryl , imine , staudinger reaction , antibacterial activity , lactam , ring (chemistry) , medicinal chemistry , proton nmr , chloroacetic acid , mass spectrum , stereochemistry , organic chemistry , catalysis , bacteria , ion , alkyl , biology , genetics
One‐pot synthesis of 1‐([6‐bromo‐2‐hydroxy‐naphthalen‐1‐yl]‐aryl‐phenyl)methyl)‐3‐chloro‐4‐(aryl‐phenyl)azetidin‐2‐ones has been reported in the present research work via Staudinger [2 + 2] ketene‐imine cycloaddition reaction pathway. The reaction of 1‐((Benzylideneamino)(aryl)methyl)‐6‐bromo‐naphthalen‐2‐ols with chloroacetic acid and triethylamine afforded 1‐([6‐bromo‐2‐hydroxynaphthalen‐1‐yl]aryl‐phenyl)methyl)‐3‐chloro‐4‐(aryl‐phenyl)azetidin‐2‐ones. For the structural elucidation of series of compounds, different analytical and spectroscopic techniques such as elemental analysis, IR spectra, 1 H‐NMR spectra and mass spectra were used. All the newly synthesized compounds were tested for their anti‐bacterial activity studies. It revealed that some of the compounds possesses moderate to good activities as compared to standard drugs. The widest spectrum of anti‐bacterial activities against both gram‐positive and gram‐negative bacterial strains among the examined compounds possessed having more hydroxyl group along with β‐lactam ring compared to other substituted azetidinones.