title: Synthesis of triazafluoranthenones via silver(I)-mediated nonoxidative and oxidative intramolecular palladium-catalyzed cyclizations.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Cyprus, Nicosia, Cyprus. koutenti@ucy.ac.cy
authors.forename: Panayiotis A
authors.initials: PA
authors.lastname: Koutentis
authors.forename: Georgia
authors.initials: G
authors.lastname: Loizou
authors.forename: Daniele
authors.initials: D
authors.lastname: Lo Re
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005459:Fluorides / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D009942:Organometallic Compounds; D018030:Silver Compounds; C105022:silver fluoride; D010165:Palladium; D005459:Fluorides