Synthesis of Benzo-Fused Heterocycles by Intramolecular alpha-Arylation of Ketone Enolate Anions
A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular alpha-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pend...
| Autores: | , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2012 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/10963 |
| Acceso en línea: | http://hdl.handle.net/11336/10963 |
| Access Level: | acceso abierto |
| Palabra clave: | Benzo-Fused Heterocycles Srn1 Reactions Ketone Enolate Anions Arylation Alpha-Aryl Ketone https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular alpha-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular CAr-CAr coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed |
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