Abstract
4-Hydroxycoumarin derivatives possessing an acid amide group in the terminal end of acyl side chain in 3-position were prepared and submitted to antibacterial tests. These derivatives were prepared by the amination of 3-(ω-carboxyacyl)- and 3-(ω-ethoxycarbonylacyl)-4-hydroxycoumarins to the objective 3-(ω-carbamoylacyl)-4-hydroxycoumarins. The interesting phenomenon observed during this amination is that the oxygen atom of the carbonyl in α-position of 3-acyl group is extremely active and is easily substituted with an imino group when 3-(ω-ethoxycarbonylacyl)-4-hydroxycoumarin is reacted with conc. ammonia water to form 3-(α-imino-ω-ethoxy-carbonylalkyl) derivative, followed by the reaction of the terminal ethoxycarbonyl group, affording 3-(α-imino-ω-carbamoylalkyl)-4-hydroxycoumarin. However, none of these α-imino and acid amide derivatives showed any marked antibacterial activity.
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