Schiff Bases from TRIS and Formylpyridines: Structure and Mechanistic Rationale Aided by DFT Calculations

[摘要]：This paper describes the synthesis and structural elucidation of 1,3-oxazolidines derived from tris(hydroxymethyl)aminomethane (TRIS) and pyridine-based aldehydes. Divergent results were obtained with other formylpyridines, such as pyridoxal, in which intramolecular hydrogen-bonding largely stabilizes the iminic structure. The oxazolidines may undergo ring-opening under acetylating conditions to afford imines through different mechanistic pathways, which have also been evaluated by DFT calculations.

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