The synthesis of benzofurane substituted ?,ß-unsaturated ketones and their derivatives

In this study, chalcones (?,ß-unsaturated ketones) were synthesized with Claisen-Schmidt condensation of 1-(1-benzofurane-2-yl) ethanone (starting compound) and different aldehyde derivatives; benzaldehyde, 2-hydroxy benzaldehyde, 3-hydroxy benzaldehyde, salicyl aldehyde, terephthaldehyde, thiophene-2-carboxaldehyde, 2-fluorobenzaldehyde, 3-fluorobenzaldehyde, 5-bromo salicyl aldehyde, 2-furaldehyde, pyrrole-2-carboxaldehyde, 4-dimethylamino benzaldehyde, 3-nitro benzaldehyde in the presence of NaOH as base.Three aldehyde derivatives; 4-hydroxy benzaldehyde, terephthaldehyde and vanilin weren?t reacted with this method. Therefore, a different method was used so as to obtain to chalcones of this three aldehyde derivatives. In this method, BF3.Et2O complex was used as catalyst.?-Haloesters containing moiety chalcone were synthesized from the reaction of substituted hydroxyl chalcones with different acylating agents; chloroacetyl chloride, bromoacetyl bromide and methacryloyl chloride in the presence of Et3N.2-Pyrazoline derivatives were obtained from the reaction of the chalcones with hydrazine monohydrate. ?-haloamides containing moiety pyrazoline were synthesized from the reaction of the pyrazoline derivatives with chloro acetylchloride in the presence of Et3N.The chemical structures of all the compounds were identified by FT-IR, 1H and 13C-NMR spectroscopic techniques. Melting point and elemental analyses values of these compounds were also determined.