A different route to the synthesis of 9,10-disubstituted phenanthrenes
We here report the synthesis of 10-aryl-9-hydroxy- and 10-aryl-9- aminophenanthrenes by reaction of the anions of 9-phenanthrol and 9-aminophenanthrene, respectively, with aryl halides (iodobenzene, 4-iodoanisole, 9-bromophenantrene). Good yields of 9,10-disubstituted phenanthrenes were obtained in...
| Autores: | , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2005 |
| País: | Argentina |
| Recursos: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/115642 |
| Acesso em linha: | http://hdl.handle.net/11336/115642 |
| Access Level: | acceso abierto |
| Palavra-chave: | Aminofenantrenos Hidroxifenantrenos Sintesis ET https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Resumo: | We here report the synthesis of 10-aryl-9-hydroxy- and 10-aryl-9- aminophenanthrenes by reaction of the anions of 9-phenanthrol and 9-aminophenanthrene, respectively, with aryl halides (iodobenzene, 4-iodoanisole, 9-bromophenantrene). Good yields of 9,10-disubstituted phenanthrenes were obtained in these reactions (>75% and ∼50% for the 9-amino and 9-hydroxyphenanthrene rings, respectively). Extension of the procedure to the reaction of both anions with o-dihalobenzenes leads to the synthesis of the ring closure products (aza- or oxa-indeno[1,2-l]phenanthrene), which bear a pentacyclic aromatic condensed ring system, although in lower overall yields (∼35%). © 2005 American Chemical Society. |
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