A new synthetic procedure is presented for the 2,3-dihydroxybenzamidation of azaalkanes. Four equivalents of 2,3-dioxomethylene (or 2,3-dimethoxybenzoyl chloride) reacted with 1,4,8,1l-tetraazacyclotetradecane (1) or 1,5,9,13-tetraazacyclohexadecane ( 2 ) to produce the corresponding cyclotetraamides (3,4,5). Subsequent treatment with either BBr3 or BCI3 in CHzCl2 solution gave the desired N,N',N'',N"'-tetra(2,3-dihydroxybenzoyl)tetraazacyclotetradecane ( 6 ) or -hexadecane (7). The latter two compounds are the first products of a new biomimetic design concept for the preparation of selective actinide-ion sequestering agents. Preliminary data indicate that the formation constant for Pu(IV) with deprotonated 6 is greater than IO5*.