Synthesis of 6-Alyl-8-Methoxy-3-Propyl-1,3-Benzoxazine and 4-Alyl-6-(Dimetilamino)Methyl-2-Methoxy Phenol from Eugenol through Mannich Reaction and Antibacterial Activity Test

Abstract

: 6-alyl-8-methoxy-3-propyl-1,3-benzoxazine and 4-alyl-6-(dimethylamino) methyl-2-methoxy phenol compounds have been synthesized through the Mannich reaction. The 6-alyl-8-methoxy-3-propyl-1,3-benzoxazine compound was synthesized by reacting eugenol, 37% formaldehyde, and propylamine under conditions of reflux with ethanol solvents at 78ºC for 6 hours obtained compounds of 6,116 grams (82.54%). The formation of 6-alyl-8-methoxy-3-propyl-1,3-benzoxazine compound characterized by FT-IR obtained CN stretching vibration at wave number 1242.16 cm-1 and peak molecular ion m/e 247 through GC-MS analysis. The 4-alyl-6-(dimethylamino) methyl-2-methoxy phenol compound was synthesized by reacting eugenol, 37% formaldehyde, and 40% dimethylamine under reflux conditions with ethanol solvents at 78ºC for 90 minutes and obtained compounds of 5,728 grams (86.39%). 4-alyl-6-(dimethylamino) methyl-2-methoxy phenol compound characterized by FT-IR obtained CN and OH stretch vibrations at wave numbers 1242.16 cm-1 and 3410.15 cm-1 and molecular ion peaks m/e 221 through GC-MS analysis. Then the two antibacterial activity tests were carried out on the two compounds using Streptococcus mutans and Escherichia coli bacteria with various concentrations of 10%, 20%, and 30%. The results obtained showed that the 6-alyl-8-methoxy-3-propyl-1,3-benzoxazine and 4-alyl-6-(dimethylamino) methyl-2-methoxy phenol compounds were classified as strong antibacterial.