Categories: Synthesis of N-Heterocycles >
Synthesis of 2-imidazolines
Recent Literature

An efficient preparation of 2-imidazolines was achieved from aldehydes and
ethylenediamines in the presence of tert-butyl hypochlorite. By this
method, 1,3-bis(imidazolin-2-yl)benzene and 2,6-bis(imidazolin-2-yl)pyridine,
which act as chiral ligands, could be prepared directly from the corresponding
dialdehydes in high yields.
M. Ishihara, H. Togo, Synthesis, 2007,
1939-1942.

2-Imidazolines were easily prepared in good yields from the reaction of
aldehydes and ethylenediamine with iodine in the presence of potassium carbonate.
The 2-imidazolines were smoothly oxidized to the corresponding imidazoles in
good yields using (diacetoxyiodo)benzene at room temperature.
M. Ishihara, H. Togo, Synlett,
2006, 227-230.

Various 2-oxazolines were prepared from aromatic aldehydes and 2-aminoethanol
with pyridinium hydrobromide perbromide in water at room temperature. The
reaction of aromatic aldehydes with ethylenediamine gave 2-imidazolines in good
yields under the same reaction conditions.
S. Sayama, Synlett,
2006, 1479-1484.

A mild reaction of α,α-difluoroalkyl amines with β-amino alcohols, β-amino thiols, and β-diamines
affords the
corresponding oxazoline, thiazoline, and imidazoline derivatives, respectively. The
conditions are
applicable for the synthesis of optically active heterocyclic compounds.
T. Fukuhara, C. Hasegawa, S. Hara, Synthesis, 2007,
1528-1534.

A very simple and efficient, microwave-assisted procedure is reported for the
synthesis of 1,3-diarylimidazolinium chlorides by cyclization of N,N′-diarylethylenediamines
dihydrochlorides with triethyl orthoformate.
A. Aidouni, A. Demonceau, L. Delaude, Synlett,
2006, 493-495.
