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Synthesis of 2-imidazolines

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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.