Premium
Schiff Bases from TRIS and Formylpyridines: Structure and Mechanistic Rationale Aided by DFT Calculations
Author(s) -
Martínez R. Fernando,
Ávalos Martín,
Babiano Reyes,
Cintas Pedro,
Jiménez José L.,
Light Mark E.,
Palacios Juan C.,
Pérez Esther M. S.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000922
Subject(s) - chemistry , tris , intramolecular force , hydroxymethyl , hydrogen bond , pyridine , ring (chemistry) , computational chemistry , stereochemistry , combinatorial chemistry , molecule , organic chemistry , biochemistry
Abstract 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 aspyridoxal, 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.