Convenient Synthesis of 7<i>H</i>-Naphtho-[1,8-<i>gh</i>]quinolin-7-one

Sawada, Tadanobu; Ishii, Hiroyuki; Aoyama, Yoshitomo; Ueda, Toyotoshi; Aoki, Junji; Takekawa, Minoru

doi:10.1080/00397911.2010.531368

Cited by 4 publications

(1 citation statement)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Under the catalysis of ZnCl 2 , 5 was obtained from the reaction of 3 and 4 and further underwent amination to afford precursors 6 and 6′ , which was then treated with glycol and H 2 SO 4 to furnish a pair of isomers 7 and 8 with bromo atoms located at the 3- or 4-position of the azabenzanthrone core respectively, enabling further modification. 35 , 36 The coupling reaction of the mixture of 7 and 8 with diphenylamine catalyzed by Pd(OAc) 2 produces isomers 1a and 1b with different polarities, which can be isolated by chromatography. Similarly, compounds 2a and 2b were synthesized and isolated (Scheme S1 † ).…”

Section: Resultsmentioning

confidence: 99%

Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging

Zang

et al. 2018

Chem. Sci.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging

Zang

et al. 2018

Chem. Sci.

View full text Add to dashboard Cite

show abstract

Vielseitige Farbstoffsynthesen durch mehrfache Kondensationsreaktionen von Acetylanilinen mit Perylenanhydriden

Jänsch

Chen

et al. 2015

Angewandte Chemie

View full text Add to dashboard Cite

Mit der Transformation von Rylenen zu neuen Chromophorfamilien wird ein weiterer Schlüsselschritt der Rylenchemie vorgestellt. Die Imidierung von Rylenanhydriden mit 2-Acetylanilinen kann durch die Wahl des Lçsungsmittels dahingehend gesteuert werden, dass eine Umsetzung entweder zu einer 4-Hydroxychinolin-(4-HQ) oder einer 4-Oxochinolineinheit (4-OQ) erfolgt. Das 4-HQ-Motiv enthält eine Aminoenongruppe, die durch eine intramolekulare Aldolkondensation gebildet wird und damit das erste vinyloge Rylenimid darstellt. Das Konzept der Vinylogisierung wird durch die Verwendung von 2,6-Diacetylanilin weiter entwickelt, wodurch ein 3a-Aza-1,6-phenalendion-erweitertes Rylengerüst mit vollständig eingebettetem Stickstoffatom erhalten wird. Durch Funktionalisierung der Aminoenonfunktionen, z. B. durch Malonsäuredinitriladdition, kçnnen die optischen und elektronischen Eigenschaften weiter modifiziert werden.

show abstract

Versatile Colorant Syntheses by Multiple Condensations of Acetyl Anilines with Perylene Anhydrides

Jänsch

Chen

et al. 2015

Angew Chem Int Ed

View full text Add to dashboard Cite

We report a key step forward in rylene chemistry: the transformation of rylenes into novel chromophore families. The imidization of rylene anhydrides with 2-acetyl anilines could be controlled by the choice of the solvent, thus causing a transformation into either a 4-hydroxyquinoline (4-HQ) or a 4-oxoquinoline (4-OQ) unit. The 4-OQ motif contains an aminoenone group formed by intramolecular aldol condensation and is the first vinylogous rylene imide. The concept of vinylogy was further developed by utilizing 2,6-diacetyl aniline leading to an 3a-aza-1,6-phenalenedione-extended rylene skeleton fully embracing the nitrogen atom. By functionalization of the aminoenone motifs, for example, malononitrile addition at the carbonyl groups, the optical and electronic properties could be further tuned.

show abstract

Convenient Synthesis of 7H-Naphtho-[1,8-gh]quinolin-7-one

Cited by 4 publications

References 15 publications

Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging

Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging

Vielseitige Farbstoffsynthesen durch mehrfache Kondensationsreaktionen von Acetylanilinen mit Perylenanhydriden

Versatile Colorant Syntheses by Multiple Condensations of Acetyl Anilines with Perylene Anhydrides

Contact Info

Product

Resources

About