Abstract
Pyridine- N-oxide-2-carbaldehyde ( 4a) was converted to the corresponding imine ( 5a) by treatment with 2,6-diisopropylaniline. Subsequent reduction with a sodium borohydride gave the corresponding ( N-arylaminomethyl)pyridine- N-oxide derivative ( 6a). A series of analogous compounds was prepared starting from the respective (aldimino)quinoline- N-oxide ( 4b) or (ketimino)pyridine- N-oxide ( 10) systems. Deprotonation of the (aminomethyl)pyridine- N-oxides resulted in a series of unexpected reactions, such as coupling, internal redox reactions or fragmentation. Eventually, the N,O-chelate aluminum complexes ( 22, 23) derived from the (aminoethyl)pyridine- N-oxide ligand systems could be obtained by treatment of the respective iminopyridine- N-oxides with trimethylaluminum. Many products were characterized by X-ray diffraction.
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