Catalyst-free microwave-assisted azo-Povarov reaction of N-carbonyl aryldiazenes with trans-cyclooctene to access ring-fused cinnoline derivatives
A previously unprecedented azo-Povarov reaction between N-carbonyl aryldiazenes and trans-cyclooctene has been developed. The participation of these aryldiazenes in the uncatalyzed [4 + 2] annulation reaction has enabled the construction of a variety of appealing fused cinnoline derivatives, with yi...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Universidad del País Vasco |
| Repositorio: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/75296 |
| Acceso en línea: | http://hdl.handle.net/10810/75296 |
| Access Level: | acceso abierto |
| Palabra clave: | N-carbonyl aryldiazenes azo-Povarov trans-cyclooctene catalyst-free cinnoline derivatives |
| Sumario: | A previously unprecedented azo-Povarov reaction between N-carbonyl aryldiazenes and trans-cyclooctene has been developed. The participation of these aryldiazenes in the uncatalyzed [4 + 2] annulation reaction has enabled the construction of a variety of appealing fused cinnoline derivatives, with yields ranging from 34% to 91% across a broad substrate scope. The starting materials are cost-effective and readily accessible, while the reaction conditions and procedures are straightforward, requiring no external catalysts. Moreover, the synthetic significance of this methodology has been demonstrated through a gram-scale azo-Povarov reaction and further derivatizations of the resulting N-containing heterocycles. |
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