Abstract: A series of functionalized 2,5-dihydro-1-hydroxy-2-R(1)-2-R(2)-4-R(3)-imidazoles were prepared by cyclocondensation of alpha-oxo hydroxylamines with ketones R(1)R(2)C=O in the presence of ammonia (R(1) = R(2) = 2-pyridyl, 4,5-diazafluoren-9-ylene, R(3) = Me; R(1) = CH(2)OCOMe, CH(2)OCOPh, 2-thienyl, CH2OH, CO2K, R(2) = R(3) = Me; R(1) = Py, R(2) = Me, R(3) = Ph; R(1) = R(2) = CH(2)OCOPh, CH2OH, R(3) = Me) and oxidized to the corresponding nitroxide radicals. The structures of 2',5'-dihydro-1'-hydroxy-4',5',5'-trimethylspiro[4,5-diazafluoren-9,2'-imidazole] (2) and of 2-(acetoxymethyl)-2,5-dihydro-2,4,5,5-tetramethylimidazole-1-oxyl (14) were determined by X-ray diffraction. In the crystal 2 forms one-dimensional chains through hydrogen bonding between N atoms of the hydroxylamine and imidazoline groups.

Cite: Hintermaier F. , Volodarsky L.B. , Polborn K. , Beck W.
New 2,5-dihydroimidazole-1-oxyls with functional side groups (N, O, S donors)
Liebigs Annales. 1995. N12. P.2189-2194. WOS

Identifiers:

Web of science:

WOS:A1995TL72700014

Citing:

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