A different route to the synthesis of 9,10-disubtituted phenanthrenes

TEMPESTI, TOMAS C.; PIERINI, ADRIANA B.; BAUMGARTNER, MARIA T.

JOURNAL OF ORGANIC CHEMISTRY

American Chemical Society

Lugar: washington, DC; Año: 2005 vol. 70 p. 6508 - 6508

0022-3263

p class="BDAbstract" style="MARGIN: 18pt 0cm">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, altho