Design, synthesis, and spectroscopic study of some new flavones containing two azo linkages

Abstract

In the present study; 5-(4-chlorophenyl azo) -2-hydroxy acetophenone (1) was prepared by diazotization of 4-chloro aniline and its coupling reaction with 2-hydroxy acetophenone, then reacted with different azo benzyloxy benzaldehydes(3a-i) to give new synthesized 2-hydroxy chalcones(4a-i). The later compounds were subjected to oxidative cyclization by catalytic amount of I2 in DMSO affording the target molecules new flavones bearing two azo-linkages (5a-i). The structures of the newly synthesized compounds were identified on the bases of their FT-IR, 1H-NMR, 13C-NMR and DEPT-135 spectra. The synthesized Flavone derivatives were evaluated against two types of bacteria gram positive (Staphylococcus aurous) and gram negative (Pseudomonas aeruginosa). The results showed that most of the synthesized flavones are more sensitive against (G -ve) bacteria than (G +ve) bacteria.