Synthesis of dioxazaborocines from N-substituted-bis(2-hydroxyaryl)aminomethylamines

The preparation of a number of tripodal amines from aminoalkylation of 1,3-benzoxazines by phenols is presented. A series of ligands prepared in this manner were successfully coordinated to boron, giving dioxazaborocines. X-ray crystal structures of two analogues are reported. These compounds are capable of releasing borate ions and are therefore potentially biologically active.