The first example of the use of 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl in the Mannich reaction to obtain radical-labeled bispidines

The first example of the use of 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl in the Mannich reaction to obtain radical-labeled bispidines Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 5, Pages: 1460-1464 Pages count : 5 DOI: 10.1007/s11172-024-4266-y

Authors

Medved’ko A.V. ¹ , Ermakov M.O. ² , Vatsadze S.Z. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

Bispidine containing a paramagnetic group was obtained for the first time by the Mannich reaction using the 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO) free radical as a reagent. The structure of the target compound, tert-butyl 9-oxo-7-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate, was confirmed by mass spectrometry and ESR spectroscopy, the molecular and crystal structure was established by X-ray diffraction analysis. In the synthesis of the starting 4-amino-TEMPO by the reductive amination reaction, the by-product of the further reaction of 4-amino-TEMPO with the starting ketone, the free biradical N-(2,2,6,6-tetramethyl-1-oxylpiperidin-4-yl)-2,2,6,6-tetramethyl-4-aminopiperidine-1-oxyl, was isolated and structurally characterized.

Medved’ko A.V. , Ermakov M.O. , Vatsadze S.Z.
The first example of the use of 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl in the Mannich reaction to obtain radical-labeled bispidines
Russian Chemical Bulletin. 2024. V.73. N5. P.1460-1464. DOI: 10.1007/s11172-024-4266-y WOS Scopus OpenAlex

Web of science:	WOS:001252371600039
Scopus:	2-s2.0-85196352360
OpenAlex:	W4399899314

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