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| Campo DC | Valor | Lengua/Idioma |
|---|---|---|
| dc.provenance | Universidad Nacional de Rosario.RepHipUNR | - |
| dc.creator | Simonetti, Sebastián Osvaldo | - |
| dc.creator | Larghi, Enrique Leandro | - |
| dc.creator | Kaufman, Teodoro Saúl | - |
| dc.date | 2016-01-26 | - |
| dc.date | 2016-01-26 | - |
| dc.date.accessioned | 2019-07-15T19:04:52Z | - |
| dc.date.available | 2019-07-15T19:04:52Z | - |
| dc.date.issued | 2016-01-26 | - |
| dc.date.issued | 2016-01-26 | - |
| dc.identifier | 1477-0520 | - |
| dc.identifier | http://hdl.handle.net/2133/10489 | - |
| dc.identifier | http://hdl.handle.net/2133/10489 | - |
| dc.identifier.uri | http://rodna.bn.gov.ar/jspui/handle/bnmm/570824 | - |
| dc.description | 5-Hydroxy-4-aryl-3,4-dihydro-1H-quinolin-2-ones are a small family of natural products isolated from fungal strains of Penicillium and Aspergillus. Most of its members, which are insecticides and anthelmintics, carry an isoprenoid C-6 side chain. The synthesis of a 6-propenyl-substituted advanced intermediate for the total synthesis of these natural products is presented in this paper. This was achieved through the stereoselective construction of a β,β-diarylacrylate derivative from 6-nitrosalicylaldehyde, using a Wittig olefination and a Heck–Matsuda arylation, followed by a selective Fe0-mediated reductive cyclization. Installation of the 6-propenyl side chain was performed by 5-O-allylation of the heterocycle, followed by Claisen rearrangement and conjugative migration of the allyl double bond, as the key steps. The Grubbs II-catalyzed olefin cross metathesis of the 6-allyl moiety with 2-methylbut-2-ene to afford a precursor of peniprequinolone is also reported. | - |
| dc.description | Fil: Simonetti, Sebastián Osvaldo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. | - |
| dc.description | Fil: Larghi, Enrique Leandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. | - |
| dc.description | Fil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina. | - |
| dc.format | application/pdf | - |
| dc.language | eng | - |
| dc.publisher | Royal Society of Chemistry | - |
| dc.relation | Información complementaria: Selected spectra of intermediates and the final product. Ver el DOI: 10.1039/c5ob02680f | - |
| dc.relation | Corrección disponible: http://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB90030E#!divAbstract | - |
| dc.relation | DOI: 10.1039/C5OB02680F | - |
| dc.relation | http://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02680f#!divAbstract | - |
| dc.rights | info:eu-repo/semantics/openAccess | - |
| dc.source | reponame:RepHipUNR (UNR) | - |
| dc.source | instname:Universidad Nacional de Rosario | - |
| dc.source | instacron:UNR | - |
| dc.source.uri | http://hdl.handle.net/2133/10489 | - |
| dc.subject | Bioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-ones | - |
| dc.subject | Natural Products | - |
| dc.subject | Metathesis | - |
| dc.subject | Precursor of Peniprequinolone | - |
| dc.title | A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones | - |
| dc.type | info:eu-repo/semantics/article | - |
| dc.type | info:eu-repo/semantics/publishedVersion | - |
| dc.type | artículo | - |
| dc.type | info:ar-repo/semantics/articulo | - |
| Aparece en las colecciones: | Universidad Nacional de Rosario. RepHipUNR | |
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