Reaction of isatin with alkylating agents with acidic methylenes
The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solventsleads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads tocompetitive formation of the corresponding epoxide 5. The formation of 5 is favored by lo...
| 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:11336/198422 |
| Acceso en línea: | http://hdl.handle.net/11336/198422 |
| Access Level: | acceso abierto |
| Palabra clave: | 4-QUINOLINONES EPOXYOXINDOLES ISATIN N- AND O-ALKYL DERIVATIVES REARRANGEMENT https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solventsleads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads tocompetitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0?5 C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products. |
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