Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: Solvent-free microwave-assisted stereoselective synthesis and theoretical calculations
Maiuolo, L. ; Merino, P. (Universidad de Zaragoza) ; Algieri, V. ; Nardi, M. ; Di Gioia, M.L. ; Russo, B. ; Delso, I. (Universidad de Zaragoza) ; Tallarida, M.A. ; De Nino, A.
Resumen: The spiro-oxindoles have found wide application because of their antiviral properties. However, in the literature few examples of synthesis of their precursors, oxindole-nitrones, are reported. In this paper, we initially present a rapid and efficient synthetic approach to ketonitrones by solvent-free microwave-assisted reaction between isatin or indanone derivatives and various hydroxylamines. The synthetic protocol is facile, clean, fast, high-yielding and stereoselective. Then, we explored the possibility to synthesize nucleobase-containing spiro-isoxazolidines with isatin and indanone nuclei by solvent-free MW-assisted 1, 3-dipolar cycloaddition, obtaining good results in yields (74-85%), and regio- and diastereoselectivity. Theoretical calculations were done to analyze the difference of reactivity of isatin and indanone derivatives with hydroxylamines.
Idioma: Inglés
DOI: 10.1039/c7ra09995a
Año: 2017
Publicado en: RSC Advances 7, 77 (2017), 48980-48988
ISSN: 2046-2069
Factor impacto JCR: 2.936 (2017)
Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 71 / 171 = 0.415 (2017) - Q2 - T2
Factor impacto SCIMAGO: 0.863 - Chemistry (miscellaneous) (Q1) - Chemical Engineering (miscellaneous) (Q1)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E10
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes.
Exportado de SIDERAL (2019-07-09-12:25:39)
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Idioma: Inglés
DOI: 10.1039/c7ra09995a
Año: 2017
Publicado en: RSC Advances 7, 77 (2017), 48980-48988
ISSN: 2046-2069
Factor impacto JCR: 2.936 (2017)
Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 71 / 171 = 0.415 (2017) - Q2 - T2
Factor impacto SCIMAGO: 0.863 - Chemistry (miscellaneous) (Q1) - Chemical Engineering (miscellaneous) (Q1)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E10
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. Exportado de SIDERAL (2019-07-09-12:25:39)
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Record created 2018-04-12, last modified 2019-07-09