Aminomethylation of trifunctional 2.5-dihydroxyacetophenone (2.5-DHA) and 2.4-dihydroxyacetophenone (2.4-DHA) by free primary and secondary amines in the presence of formaldehyde has been conducted for the first time. It has been established that 2.5-DHA is aminomethylated with secondary heterocyclic amines - piperidine and morpholine and with aqueous formaldehyde solution in alcohol medium at 500C. The reaction proceeds simultaneously via all three functions forming stable C,O-substitution products − β-amino-2-aminomethoxy-4-aminomethyl-5-hydroxypropiophenones. The aminomethylation reaction of 2.4-DHA proceeds by phenolic function only under the action of methylene bis-amines piperidine and morpholine in absolute alcohol at 200C with the formation of 2.4-dihydroxy-3-aminomethylacetophenones. Aminomethylation of 2.4-DHA with primary aromatic amines - n-toluidine and n-anisidine proceeds in absolute alcohol under the action of formaldehyde in the form of paraform in the presence of catalytic amounts of KOH at 500C. The reaction products are 3.4-dihydro-2H-1.3-benzoxazines. 2.5-DHA does not react with primary aromatic amines and formaldehyde. The composition and structure of compounds synthesized have been established according to the data of elemental and spectral methods of analysis
doi.org/10.32737/0005-2531-2022-3-81-86