- 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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supporting information
p. 5417 - 5422
(2020/07/08)
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- Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
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The reaction of various organozinc pivalates with anthranils provides anilines derivatives, which cyclize under acidic conditions providing condensed quinolines. Using alkenylzinc pivalates, electron-rich arylzinc pivalates or heterocyclic zinc pivalates produces directly the condensed quinolines of which several structures belong to new heterocyclic scaffolds. These N-heterocycles are of particular interest for organic light emitting diodes with their high photoluminescence quantum yields and long exciton lifetimes as well as for hole-transporting materials in methylammonium lead iodide perovskites solar cells due to an optimal band alignment for holes and a large bandgap.
- Li, Jie,Tan, Eric,Keller, Niklas,Chen, Yi-Hung,Zehetmaier, Peter M.,Jakowetz, Andreas C.,Bein, Thomas,Knochel, Paul
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supporting information
p. 98 - 103
(2019/01/08)
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- Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole
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A nitrogen-iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a nonsteroidal anti-inflammatory drug) were efficiently established through this protocol.
- Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
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p. 216 - 219
(2018/01/17)
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- Nitrogen anthracene class compound and its synthetic method and application (by machine translation)
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The invention discloses a formula (2) shown in nitrogen anthracene class of compound and its synthetic method, high Iodized salt as reaction raw material, in the inorganic nitrogen reagent, additive, water, alkali, under the action of the metal catalyst, in the 80 - 150 °C conditions, reacts in a solvent 12 - 60 hours to obtain various nitrogen anthracene class compounds. The invention by post method of introducing nitrogen atoms, to avoid the early stage in the reaction of the nitrogen heterocyclic to metal catalyst of the reaction conditions such as not compatibility; in addition, high Iodized salt in the full utilization of the two aryl, shows that the method of the invention atom economy. Prepared by the method of the invention can be further applied [...] compound of the fluorescent indicator acridine orange synthesis. (by machine translation)
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Paragraph 0107-0110
(2018/05/16)
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- Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines
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[Figure not available: see fulltext.] Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]-acridines. Substituent at the triple bond governs a choice between transition metal or Br?nsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the o-aryl(phenylethynyl) fragment. PtCl2 efficiently catalyzes cyclization of 2-aryl-3-ethynylhetarenes.
- Shestakov, Aleksandr N.,Pankova, Alena S.,Kuznetsov, Mikhail A.
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p. 1103 - 1113
(2017/12/08)
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- Preparation method of multi-functional group acridine compound and derivative thereof
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The present invention relates to a preparation method of a multi-functional group acridine compound and a derivative thereof. According to the present invention, specifically a bisphosphine ligand and palladium complex catalyzed series connection coupling/cyclization reaction is used to prepare the acridine compound represented by a formula I, wherein various groups are defined in the specification; and the method has advantages of mild reaction condition, simple operation and wide substrate applicability, and the multi-functional group acridine compound and the derivative thereof can be prepared in the high yield manner. The formula I is defined in the specification.
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Paragraph 0145; 0146; 0148; 0149; 0174; 0175; 0176; 0177
(2017/02/17)
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- Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol
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A facile and efficient approach for the synthesis of a variety of acridines via the tandem coupling/cyclization of substituted 2-bromobenzaldehydes and anilines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Pd2(dba)3 and diphosphine ligand dppf, providing a broad range of substituted acridines in good to excellent yields (up to 99%). The Lewis acid, AlCl3, is required to promote the cyclization for less electron-rich anilines.
- Wang, Ting-Jun,Chen, Wen-Wen,Li, Yi,Xu, Ming-Hua
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p. 6580 - 6586
(2015/06/16)
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- Facile synthesis of acridine derivatives by ZnCl2-promoted intramolecular cyclization of o -arylaminophenyl schiff bases
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A concise and efficient method for the synthesis of a wide range of acridine derivatives and polycyclic aza-aromatic compounds from a ZnCl 2-promoted cyclization reaction of readily available o-arylaminophenyl Schiff base compounds under convenient conditions was developed. Reaction conditions and scope of the new method were examined in detail.
- Su, Qing,Li, Pei,He, Mina,Wu, Qiaolin,Ye, Ling,Mu, Ying
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supporting information
p. 18 - 21
(2014/01/23)
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- Preparation of aza-polycyclic aromatic compounds via superelectrophilic cyclizations
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(Chemical Equation Presented) Alkenyl-substituted N-heterocycles react in superacidic CF3SO3H (triflic acid) to produce dicationic intermediates. These superelectrophiles undergo cyclizations to give varied aza-polycyclic aromatic compounds in generally good yields (27-99%, 16 examples). Theoretical calculations indicate a preference for charge-separated dicationic intermediates.
- Li, Ang,Gilbert, Thomas M.,Klumpp, Douglas A.
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p. 3654 - 3657
(2008/09/20)
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- Charge migration in dicationic electrophiles and its application to the synthesis of aza-polycyclic aromatic compounds
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Superacid-promoted reactions of dicationic electrophiles have been studied, and the positive charge centers are found to migrate apart in a predictable manner. Using isotopic labeling the charge migration is found in one system to occur through successive deprotonation-reprotonation steps. The charge migration chemistry is the basis for new general synthetic route to aza-polycyclic aromatic compounds.
- Li, Ang,Kindelin, Patrick J.,Klumpp, Douglas A.
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p. 1233 - 1236
(2007/10/03)
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- Synthesis of trans-3,4-Dihydroxy-3,4-dihydrobenz- and -acridines, Possible Proximate Carcinogenic Metabolites of Polycyclic Azaarenes
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The vicinal trans-3,4-dihydro 3,4-diols of benz- and -acridine have been synthesized via modified Birch reduction of the parent heterocycles.Thus the pyridine moiety and the angular benzene ring could be reduced selectively.Controlled reoxidation re-formed the stable acridine part, leaving the angular ring partially hydrogenated.Isomerization of the isolated double bond led to 1,2-dihydrobenzacridines as key intermediates of the synthesis.Prevost reaction, bromination, dehydrobromination, and hydrolysis of the 3,4-dihydrodioldiacetates in the angular ring didnot interfere with the basic acridine moiety.This strategy has been applied to both series, i.e., benz- and -acridine.In some reaction steps the product ratio and total yield were strongly influenced by the position of nitrogen, indicating intrinsic differences in the chemical reactivity of the two systems.The new title compounds which have not been prepared previously are presumably the proximate carcinogenic metabolites of benzacridines.The benzacridines were chosen as model compounds of polycylcic azaarenes (PAA) which impose an increasing environmental risk with the industrial processing of synthetic fuel from shale and oil.
- Schaefer-Ridder, Maria,Engelhardt, Ulrich
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p. 2895 - 2899
(2007/10/02)
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