Intramolecular 1,3-Dipolar Cycloaddition of Alkenylnitrones of the 4H-Imidazole Series: Synthesis of a New Nitroxide pH-Sensitive Spin Probe

Intramolecular 1,3-Dipolar Cycloaddition of Alkenylnitrones of the 4H-Imidazole Series: Synthesis of a New Nitroxide pH-Sensitive Spin Probe Full article

Journal

Synthesis
ISSN: 0039-7881

Output data

Year: 2010, Number: 2, Pages: 343-348 Pages count : DOI: 10.1055/s-0029-1217109

Tags

1,3-dipolar cycloaddition; low-valence titanium; nitroxide radical; 4H-imidazole 3-oxide; pH-sensitive spin probe

Authors

Morozov Denis A. ^1,2 , Kirilyuk Igor A. ¹ , Gatilov Yuri V. ¹ , Bagryanskaya Irina Yu. ¹ , Bozhko Julya Yu. ³ , Komarov Denis A. ³ , Grigor'ev Igor A. ¹

Affiliations

1	(Данные Web of science) Novosibirsk Inst Organ Chem SB RAS, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Inst Chem Kinet & Combust SB RAS, Novosibirsk 630090, Russia

A new method was used for the preparation of a pH-sensitive spin probe involving an intramolecular 1,3-dipolar cycloaddition - reductive isoxazolidine ring-opening - oxidation reaction sequence. 2-(2-Allyloxyphenyl)-5-R-4,4-dimethyl-4H-imidazole-3-oxides (R = Me, NMe2), prepared from 3-hydroxylamino-3-methylbutan-2-one, undergo intramolecular 1,3-dipolar cycloaddition upon heating in toluene. Treatment of the cycloadducts with low-valence titanium (LVT) reagent resulted in reductive cleavage of the N-O bond of the isoxazolidine ring to give 3'-hydroxymethyl-5,5-dimethyl-4-R-2,5-dihydrospiro[imidazol-2,4'-chromane]s. The amine ( R = NMe2) was then oxidized with MCPBA to the target nitroxide 3'-hydroxymethyl-5,5-dimethyl-4-dimethylamino-2,5-dihydrospiro[imidazole-2,4'-chroman]-1-oxyl.

Morozov D.A. , Kirilyuk I.A. , Gatilov Y.V. , Bagryanskaya I.Y. , Bozhko J.Y. , Komarov D.A. , Grigor'ev I.A.
Intramolecular 1,3-Dipolar Cycloaddition of Alkenylnitrones of the 4H-Imidazole Series: Synthesis of a New Nitroxide pH-Sensitive Spin Probe
Synthesis. 2010. N2. P.343-348. DOI: 10.1055/s-0029-1217109 WOS Scopus РИНЦ

Published online:	Nov 6, 2009
Published print:	Jan 1, 2010

Web of science	WOS:000274245900021
Scopus	2-s2.0-73949133013
Elibrary	15316930
OpenAlex	W2061477056