SYNTHESIS AND STRUCTURE OF SOME CHALCONES CONTAINING ACETAMIDE GROUP

Tóm tắt

Two chalcones including (E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one (3a) and (E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one (3b) were synthesized by the reaction of acetophenone and 2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde, respectively. The Williamson reaction of (3a) or (3b) with the various N-aryl-2-chloroacetamides gave eight (E)-N-(4-aryl)-2-(2/4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetamide compounds; seven of them were new compounds: (E)-N-(4-bromophenyl)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetamide (5a), (E)-N-(4-chlorophenyl)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetamide (5b), (E)-N-(4-methoxyphenyl)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetamide (5c), (E)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)-N-(p-tolyl)acetamide (5d), (E)-N-(4-bromophenyl)-2-(4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetamide (5e), (E)-N-(4-chlorophenyl)-2-(4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetamide (5f), (E)-N-(4-methoxyphenyl)-2-(4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetamide (5g), (E)-2-(4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)-N-(p-tolyl)acetamide (5h). The structure of the compounds was determined by their IR, 1H-NMR, 13C-NMR, and HR-MS spectral data.