Synthesis and antimicrobial activities of 2-azetidinyl-4-quinazolinone derivatives of diclofenac analogue

A new class of 2-azetidinyl-4-quinazolinones 6a-k was synthesized by multi-step process, starting from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetic acid 1. Acid 1 was easily converted to acid chloride 2, which on cyclization reaction with 5-bromo anthranilic acid yielded benzoxazinone 3. The condensation reaction of 3 with benzene-1,4-diamine afforded 4-quinazolinone 4. Finally the title compound 6a-k was synthesized from 4-quinazolinone 4 by Schiff base formation 5a-k with aromatic aldehyde and then cyclization reaction with chloroacetylchloride. The in vitro antimicrobial activity of compounds 5a-k and 6a-k were tested. These compounds showed pronounced antimicrobial activity when 4-Cl and 4-OCH (3) groups were present.