posted on 2015-12-16, 19:26authored byPanayiotis A. Koutentis, Georgia Loizou, Daniele Lo Re
Silver(I) fluoride (AgF)-mediated intramolecular nonoxidative and
oxidative palladium-catalyzed cyclizations of 1,3-diphenyl- and 8-iodo-1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-ones 6a (R = H) and 7a (R = I) afford a new ‘alkaloid
like’ ring system 2-phenyl-6H-[1,2,4]triazino[5,6,1-jk]carbazol-6-one 8a (triazafluoranthenone)
in 86 and 100% yields, respectively. Furthermore, these cyclization
protocols were used to prepare triazafluoranthenone analogues 8b–e bearing dialkylamino, methoxy, and
phenylsulfanyl substituents at C-5, which were also independently
synthesized from triazafluoranthenone 8a by regioselective
nucleophilic addition. Similar AgF-mediated intramolecular nonoxidative
and oxidative palladium-catalyzed cyclizations of 8,10-dihydro-1-iodo-10-phenylphenazin-2(7H)-ones 13 gave the new ‘alkaloid like’
ring system 8H-indolo[1,2,3-mn]phenazin-8-one 14 in 80 and 18% yields, respectively.