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 t...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-08, Vol.70 (16), p.6508-6511
Main Authors: Tempesti, Tomás C, Pierini, Adriana B, Baumgartner, María T
Format: Article
Language:English
Subjects:
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary: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%).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050646f