Abstract: Spirocyclic nitroxyl radicals (SNRs) are stable paramagnetics bearing spiro-junction at alpha-, beta-, or gamma-carbon atom of the nitroxide fragment, which is part of the heterocyclic system. Despite the fact that the first representatives of SNRs were obtained about 50 years ago, the methodology of their synthesis and their usage in chemistry and biochemical applications have begun to develop rapidly only in the last two decades. Due to the presence of spiro-function in the SNRs molecules, the latter have increased stability to various reducing agents (including biogenic ones), while the structures of the biradicals (SNBRs) comprises a rigid spiro-fused core that fixes mutual position and orientation of nitroxide moieties that favors their use in dynamic nuclear polarization (DNP) experiments. This first review on SNRs will give a glance at various strategies for the synthesis of spiro-substituted, mono-, and bis-nitroxides on the base of six-membered (piperidine, 1,2,3,4-tetrahydroquinoline, 9,9 '(10H,10H ')-spirobiacridine, piperazine, and morpholine) or five-membered (2,5-dihydro-1H-pyrrole, pyrrolidine, 2,5-dihydro-1H-imidazole, 4,5-dihydro-1H-imidazole, imidazolidine, and oxazolidine) heterocyclic cores.

Cite: Zaytseva E.V. , Mazhukin D.G.
Spirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals
Molecules. 2021. V.26. N3. 677 . DOI: 10.3390/molecules26030677 WOS Scopus OpenAlex

Files: Full text from publisher

Dates:

Published online:

Jan 28, 2021

Identifiers:

Web of science:	WOS:000615457000001
Scopus:	2-s2.0-85100820442
OpenAlex:	W3126407726

Citing:

DB	Citing
Web of science	11
Scopus	10
OpenAlex	11

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