- Copper-Catalyzed N,N-Diarylation of Amides for the Construction of 9,10-Dihydroacridine Structure and Applications in the Synthesis of Diverse Nitrogen-Embedded Polyacenes
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We reported herein CuI/DMEDA catalyzed N,N-diarylation reaction of amides with various di(o-bromoaryl)methanes to produce diverse 9,10-dihydroacridine derivatives. The resulting 9,10-dihydroacridine derivatives were oxidized selectively under mild conditions to afford acridine, acridinone, and acridinium derivatives. The copper-catalyzed N,N-diarylation reaction coupled with oxidative aromatization reaction enabled the facile construction of nitrogen atom-embedded tetracenes and pentacenes of different ortho-fused patterns. The luminescence properties, especially the effect of fusion pattern on fluorescence emission of acquired N-polycenes, were also demonstrated.
- Tan, Mei-Ling,Tong, Shuo,Hou, Sheng-Kai,You, Jingsong,Wang, Mei-Xiang
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p. 5417 - 5422
(2020/07/08)
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- Synthesis of an s-Butyldibenzacridine. Alkyl Migration in the Bernthsen Reaction
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The Bernthsen reaction between N-1-naphthyl-2-naphthylamine and 2-methylbutanoic acid and its anhydride at 200-230 deg for seven hours gives a low yield of 12- or 13-s-butyldibenzacridine, instead of the expected 14-isomer.The parent molecule dibenzacridine results from the same reaction conducted at 270 deg for thirteen hours.It is suggested that alkyl migration may have occurred in some other cases where the Bernthsen reaction was reported to yield 14-alkyldibenzacridines.
- Klemm, L.H.,Chiang, Eva,O'Bannon, Gerald W.
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p. 571 - 574
(2007/10/02)
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- REGIOSELECTIVE CYCLISATION OF ANIL DERIVATIVES - A SHORT SYNTHESIS OF DIBENZACRIDINES
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Dibenzacridines have been synthesized in almost quantitative yields by regioselective thermal cyclisation of anil hydrochlorides followed by dehydrogenation.
- Kar, Gandhi K.,Karmakar, Arun Ch.,Ray, Jayanta K.
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p. 223 - 224
(2007/10/02)
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- Synthesis of trans-10,11-Dihydroxy-10,11-dihydrodibenz(a,h)acridine and Its Diastereomeric Epoxides. Possible Carcinogenic Metabolites of Dibenz(a,h)acridine
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trans-10,11-Dihydroxy-10,11-dihydrodibenz(a,h)acridine (12), (+/-)-10α,11β-dihydroxy-8α,9α-epoxy-8,9,10,11-tetrahydrodibenz(a,h)acridine (3), and 10α,11β-dihydroxy-8β,9β-epoxy-8,9,10,11-tetrahydrodibenz(a,h)acridine (4), which are potentially proximate and ultimate carcinogens of dibenz(a,h)acridine (1), are synthesized.Regiospecific oxygenation at C-11 of 8,9,10,11-tetrahydrodibenz(a,h)acridine with mercuric acetate in acetic acid resulted in an intermediate that was converted to the above dihydrodiol and diol epoxides. 1H NMR, UV, and fluorescence emission spectra of dibenz(a,h)acridine derivatives are reported.
- Kumar, Subodh
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p. 3070 - 3073
(2007/10/02)
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