Abstract
N1-(Nicotinoyl)-N2-4-(2,2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl)hydraxine was obtained by condensation of nicotinoyl hydrazide with 2,2,6,6-tetramethyl-4-oxopiperidine 1-oxyl. Acylation of 2,2,6,6-tetramethyl-4-hydroxypiperidine 1-oxyl with nicotinoyl chloride gives nicotinic acid 2,2,6,6-tetramethyl-1-oxyl 4-piperidyl ester. A spin-labeled analog of nicotinamide was obtained by condensation of nicotinoyl azide with 4-amino-2,2,6,6-tetramethylpiperidine 1-oxyl. The synthesis of 1-N-(Β-D-ribofuranoside)-3'-N[4-(2,2,6,6-tetramethylpiperidine-1-oxyl)pyridinecarboxamide from 2,2,6,6-tetramethyl-4-nicotinoylaminopiperidine 1-oxyl and 2,3,5-tri-O-benzoyl-Β-D-ribofuranosyl bromide proceeds without damage to the iminoxyl radical. The preparation of the corresponding spin-labeled nucleotide is hindered by destruction of the iminoxyl radical during ion-exchange chromatography.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 352–355, March, 1976.
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Lifshits, N.L., Mal'tsev, N.I., Yakovlev, V.A. et al. Synthesis and properties of nicotinic acid derivatives containing a 2,2,6,6- tetramethylpiperidine 1-oxyl residue. Chem Heterocycl Compd 12, 300–303 (1976). https://doi.org/10.1007/BF00479569
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DOI: https://doi.org/10.1007/BF00479569