Sc(OTf)(3)-Mediated [4+2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction
We disclose the first accomplishment of the azo-Povarov reaction involving Sc(OTf)3-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offers a rapid access to an array of cinno...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2022 |
| País: | España |
| Institución: | Universidad del País Vasco |
| Repositorio: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/58240 |
| Acceso en línea: | http://hdl.handle.net/10810/58240 |
| Access Level: | acceso abierto |
| Palabra clave: | Diels-Alder reaction topoisomerase-i inhibitors biological evaluation facile synthesis Lewis-acid heterocycles 1,2-diaza-1,3-butadienes tetrahydroquinolines cyclization antifungal |
| Sumario: | We disclose the first accomplishment of the azo-Povarov reaction involving Sc(OTf)3-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offers a rapid access to an array of cinnoline derivatives in moderate to good yields for substrates over a wide scope. The synthetic potential of the protocol was achieved by the gram-scale reaction and further derivatization of the obtained polycyclic product. |
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