Calix[n]arene-catalyzed three-component povarov reaction: microwave-assisted synthesis of Julolidines and mechanistic insights
A new one-pot cascade reaction-based application of Povarov reactions with a p-sulfonic acid calix[4]arene catalyst for the synthesis of a series of 34 julolidine derivatives with substituents at C8 or C9 in good to excellent yields is reported. These microwave-assisted reactions proceeded efficient...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2018 |
| País: | Brasil |
| Institución: | Universidade Federal de Viçosa (UFV) |
| Repositorio: | LOCUS Repositório Institucional da UFV |
| Idioma: | inglés |
| OAI Identifier: | oai:locus.ufv.br:123456789/18235 |
| Acceso en línea: | https://doi.org/10.1021/acs.joc.7b02532 http://www.locus.ufv.br/handle/123456789/18235 |
| Access Level: | acceso abierto |
| Palabra clave: | Povarov reaction Calix[n]arene-catalyzed |
| Sumario: | A new one-pot cascade reaction-based application of Povarov reactions with a p-sulfonic acid calix[4]arene catalyst for the synthesis of a series of 34 julolidine derivatives with substituents at C8 or C9 in good to excellent yields is reported. These microwave-assisted reactions proceeded efficiently, had short reaction times, were metal-free, were low cost, and used an inexpensive, easily available and nontoxic catalyst. These advantages, along with a simple workup procedure, make this protocol a very efficient and green alternative to the traditional methods for constructing these types of N- heterocyclic skeletons. In addition, this protocol allows the formation of julolidine structures, which requires the construction of four new C−C bonds and two C−N bonds. A mechanism for the Povarov reaction involving a stepwise sequence via ionic intermediates was proposed and validated. |
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