Stereoselective Synthesis of Biheterocycles Containing Indole and 5,6-Dihydropyridin-2(1H)-one or α-Methylene-β-butyrolactam Scaffolds
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Título: | Stereoselective Synthesis of Biheterocycles Containing Indole and 5,6-Dihydropyridin-2(1H)-one or α-Methylene-β-butyrolactam Scaffolds |
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Autor/es: | Salah, Kennouche | Blanco-López, Ester | Sirvent, Ana | Behloul, Cherif | Nájera, Carmen | Retamosa, Maria de Gracia | Sansano, Jose M. | Yus, Miguel | Foubelo, Francisco |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Allylation | Chiral sulfinyl imines | Dihydropyridinones | Functionalized indoles | Lactams |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 16-mar-2022 |
Editor: | Wiley-VCH GmbH |
Cita bibliográfica: | ChemistrySelect. 2022, 7(11): e202104245. https://doi.org/10.1002/slct.202104245 |
Resumen: | Indium-mediated allylation of N-tert-butanesulfinyl imines derived from indole-2 and 3-carbaldehydes 3 and 5 with allylic bromides 6, proceed with high diastereoselectivity. Homoallylic amide derivatives 13 and 14 are transformed into dihydropyridinones 15 and 16, upon successive desulfinylation, N-acylation with acryloyl chloride and ring-closing-metathesis. Desulfinylation of amine ester derivatives 17 and 18, obtained when ethyl 2-(bromomethyl)acrylate (6 b) is used as the allylating reagent, lead to the corresponding α-methylene-γ-butyrolactams 19 and 20, in modest yields. |
Patrocinador/es: | We thank the continuous financial support from the Spanish Ministerio de Economía y Competitividad (MINECO; project CTQ2016-81797-REDC, CTQ2017-85093-P), Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, PID2019-107268GB-100), FEDER, the Generalitat Valenciana (IDIFEDER/2021/013, CIDEGENT/2020/058, APOTIP/2021/020), the University of Alicante (VIGROB-068), and the Ministère de l’Enseignement Supérieur et de la Recherche Scientifique Algérienne; Direction de la Coopération et des Echanges Interuniversitaires; Programme de Formation Résidentielle à l’Étranger au titre de l’année universitaire 2019/2020: Programme National Exceptionnel (PNE). |
URI: | http://hdl.handle.net/10045/122206 |
ISSN: | 2365-6549 |
DOI: | 10.1002/slct.202104245 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2022 The Authors. ChemistrySelect published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1002/slct.202104245 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
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