ISSN:
0947-3440
Keywords:
Nitroxide radicals
;
2,5-Dihydroimidazoles
;
Hydroxylamines, secondary
;
α-Keto hydroxylamines
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A series of functionalized 2,5-dihydro-1-hydroxy-2-R1-2-R2-4-R3-imidazoles were prepared by cyclocondensation of α-oxo hydroxylamines with ketones R1R2C = O in the presence of ammonia (R1 = R2 = 2-pyridyl, 4,5-diazafluoren-9-ylene, R3 = Me; R1 = CH2OCOMe, CH2OCOPh, 2-thienyl, CH2OH, CO2K, R2 = R3 = Me; R1 = Py, R2 = Me, R3 = Ph; R1 = R2 = CH2OCOPh, CH2OH, R3 = 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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199512304
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