Synthesis and characterization of novel hybrid molecules including pyrazole and coumarin structures

In this work, the synthesis and characterization studies of novel hybrid compounds in which two bioactive nuclei such as pyrazole and coumarin are contained in one molecule are targeted. The following studies were carried out in line with this objective. In this project, α, β-unsaturated carbonyl compounds (B) containing the dimethylamino group were first synthesized from the reactions of acetophenone and 4-chloroacetophenone compounds with N,N-Dimethylformamide-dimethylacetal (DMF-DMA). By reacting the compounds B with aromatic diazonium salts at 0 °C, compounds C which are contain aldehyde group were obtained. Then, β-ketoester compounds (D) containing the pyrazole ring were synthesized from the subsequent reactions of the compounds C with ethyl 4-chloro-3-oxobutanoate reactive. In the last step, novel hybrid compounds (E) containing coumarin and pyrazole rings were obtained from reactions of compounds D with salicylaldehyde derivatives. The synthesized new compounds were characterized by elemental analysis, FTIR, NMR, HRMS.