Abstract
Starting from commercially available (hetero)aromatic nitriles
and (1R ,2R )-cyclohexane-1,2-diamine,
nine NH-imidazolines (hexahydro-1H -benzo[d ]imidazoles) were synthesized
in good yields. The molecular structures of three imidazolines were confirmed
by X-ray analysis. N-Benzylation afforded some of the desired N -benzylimidazolines, but was incompatible
with imidazolines that possessed strong electron-accepting heteroaromatic groups
at C2. In the latter cases, the products decomposed during column
chromatography to form N,N′-disubstituted cyclohexane-1,2-diamines.
Key words
heterocycles - imidazolines - chiral pool - N- benzylation - stability
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