Aromatic amine N-oxides are underutilized as organic ligands in coordination chemistry, compared to their parent compounds – aromatic amines. Similarly, Schiff base ligands, that are otherwise extremely popular as polydentate chelating ligands, rarely contain an N-oxide residue. One of these reasons is the commercial inaccessibility and the difficulty of the synthesis of 2-pyridinecarboxaldehyde N-oxide, which is the aldehyde component for the construction of the N-oxide Schiff bases. The commonly used procedure for the synthesis of 2-pyridinecarboxaldehyde N-oxide starts with the oxidation of 2-methylpyridine to its N-oxide form, followed by the selective oxidation of the methyl group with selenium dioxide. A few other synthetic methods have recently been proposed, but do not suggest an easier route of accessibility. We are presenting an accessible alternative synthetic method using the oxidation of 2-pyridinecarboxaldehyde, in the protected form of the diacetal. The diacetal form of the 2-pyridinecarboxaldehyde N-oxide can be directly used in condensation reactions with amines to form the desired pyridine N-oxide Schiff bases, or it can be deprotected to yield 2-pyridinecarboxaldehyde N-oxide. Abilities of the 2-pyridinecarboxaldehyde N-oxide diacetal to act as a ligand in transition metal complexes will also be presented. <br/>

Accessibility of 2-pyridinecarboxaldehyde n-oxide via oxidation of 2-pyridinecarboxaldehyde diacetal

256th National Meeting (2018)

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