Synthesis and Some Transformations of New Acetophenone Derivatives Containing a Carbamate Moiety

The acylation of methyl phenylcarbamate, 2-(morpholin-4-yl)ethyl phenylcarbamate, and 2-(pyri­din-2-yl)ethyl phenylcarbamate with acetic anhydride in polyphosphoric acid at 50–55°C (3 h) involved the para position with respect to the carbamate group with the formation of the corresponding acetophenones. Methyl 2-methoxyphenylcarbamate was acylated under similar conditions to give methyl 5-acetyl-2-methoxy­phenylcarbamate. Methyl 4- and 2-acetylphenylcarbamates reacted with N -bromosuccinimide in the presence of copper(II) acetate and DMF at 80°C and with HCl and HBr in the presence of DMSO in ethyl acetate at 30–33°C to afford methyl [4(2)-(2-dimethylamino-2-oxoacetyl)phenyl]carbamates and methyl [4(2)-(2-bromo-2-chloroacetyl)phenyl]carbamates, respectively. The condensation of 2-(morpholin-4-yl)ethyl and 2-(pyridin-2-yl)­ethyl (4-acetylphenyl)carbamates with 4-methoxybenzaldehyde in methanolic potassium hydroxide furnished the corresponding chalcones.