ChemInform Abstract: SYNTHESIS AND PROPERTIES OF 4‐ETHOXYFLUORANTHENOPYRYLIUM AND FLUORANTHENOPYRONE SALTS

Abstract

Das 11‐Hydroxy‐12‐acetyl‐fluoranthen (I) und in ähnlicher Weise auch das Isomere (II) werden zu Pyronen und Pyryliumsalzen cyclisiert.

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…π-Expanded fluoranthene derivatives, reported by Buu-Hoı̈ and co-workers (Chart ), include the carbazole system C47.1 , obtained from fluoranthene via Haworth-type annulation, Fischer indolization, and aromatization, and the three fused systems C47.2 – 4 , all derived from 8-aminofluoranthene. [ k ]­Fused pyrylium salts C47.5 were reported by Shenbor and Azarov in 1979 . Furans and oxazoles, such as C47.6 – 7 , were obtained in 1982 by Shechter et al via thermal and photochemical additions of acetylenes and nitriles, respectively, to diazoacenaphthenone and 2-diazoaceanthrenone …”

“…In the following decade, the Buu-Hoı̈ group synthesized a range of other fluoranthene derivatives, 171.9 , 171.10 – 13 , 171.14 , and 171.15 , which were explored as potential carcinogens. Shenbor and co-workers reported several further [ b ]­fused derivatives containing oxazole ( 171.19 – 20 ), imidazole ( 171.21 and 171.22 ), and pyrylium ( 171.23 ) moieties.…”

“…[k]Fused pyrylium salts C47.5 were reported by Shenbor and Azarov in 1979. 995 Furans and oxazoles, such as C47.6−7, were obtained in 1982 by Shechter et al via thermal and photochemical additions of acetylenes and nitriles, respectively, to diazoacenaphthenone and 2-diazoaceanthrenone. 745 Diacenaphtho[1,2-b:1′,2′-d]thiophene C47.8 is a red-colored solid obtained surprisingly simply by fusion of acenaphthene and sulfur.…”

“…The selectivity was explained in terms of Li coordination to the quinoline nitrogen. 1016 ), imidazole (171.21 1017 and 171.22 1018 ), and pyrylium (171.23 995 ) moieties.…”