Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition.
Beilstein J Org Chem
; 15: 2036-2042, 2019.
Article
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| MEDLINE
| ID: mdl-31501671
ABSTRACT
Sterically shielded nitroxides of the pyrrolidine series have shown the highest resistance to reduction. Here we report the synthesis of new pyrrolidine nitroxides from 5,5-dialkyl-1-pyrroline N-oxides via the introduction of a pent-4-enyl group to the nitrone carbon followed by an intramolecular 1,3-dipolar cycloaddition reaction and isoxazolidine ring opening. The kinetics of reduction of the new nitroxides with ascorbate were studied and compared to those of previously published (1S,2R,3'S,4'S,5'S,2â³R)-dispiro[(2-hydroxymethyl)cyclopentan-1,2'-(3',4'-di-tert-butoxy)pyrrolidine-5',1â³-(2â³-hydroxymethyl)cyclopentane]-1'-oxyl (1).
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1
Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
Beilstein J Org Chem
Año:
2019
Tipo del documento:
Article