- CONVENIENT SYNTHESIS OF 9-ALKYL AND 9-ARYLACRIDINES FROM METHYL (SEM) PROTECTED ACRIDONE
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The low yielding addition of organolithium reagents to acridone becomes a convenient high yielding route to 9-alkyl and 9-arylacridines when SEM-acridone is used.
- Zeng, Zijian,Zimmerman, Steven C.
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Read Online
- Investigation in the field of quinazolines. 8*. New reaction of N-alkylation of 4,4-diphenyl-3,4-dihydroquinazolines
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[Figure not available: see fulltext.] The reaction of substituted 4,4-diphenyl-3,4(1,4)-dihydroquinazolines with various alkylating agents in DMSO–KOH leads (depending on the structure of the alkylating agent) to the formation of the corresponding N1
- Gromachevskava, Elena V.,Kaigorogova, Elena A.,Bespalov, Alexander V.,Demidov, Oleg P.,Krapivin, Gennady D.
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Read Online
- Design, synthesis and evaluation of novel 9-arylalkyl-10-methylacridinium derivatives as highly potent FtsZ-targeting antibacterial agents
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With the increasing incidence of antibiotic resistance, new antibacterial agents having novel mechanisms of action hence are in an urgent need to combat infectious diseases caused by multidrug-resistant (MDR) pathogens. Four novel series of substituted 9-arylalkyl-10-methylacridinium derivatives as FtsZ inhibitors were designed, synthesized and evaluated for their antibacterial activities against various Gram-positive and Gram-negative bacteria. The results demonstrated that they exhibited broad-spectrum activities with substantial efficacy against MRSA and VRE, which were superior or comparable to the berberine, sanguinarine, linezolid, ciprofloxacin and vancomycin. In particular, the most promising compound 15f showed rapid bactericidal properties, which avoid the emergence of drug resistance. However, 15f showed no inhibitory effect on Gram-negative bacteria but biofilm formation study gave possible answers. Further target identification and mechanistic studies revealed that 15f functioned as an effective FtsZ inhibitor to alter the dynamics of FtsZ self-polymerization, which resulted in termination of the cell division and caused cell death. Further cytotoxicity and animal studies demonstrated that 15f not only displayed efficacy in a murine model of bacteremia in vivo, but also no significant hemolysis to mammalian cells. Overall, this compound with novel skeleton could serve as an antibacterial lead of FtsZ inhibitor for further evaluation of drug-likeness.
- Song, Di,Zhang, Nan,Zhang, Panpan,Zhang, Na,Chen, Weijin,Zhang, Long,Guo, Ting,Gu, Xiaotong,Ma, Shutao
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- Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products
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The invention particularly relates to a compound, a pharmaceutical composition, a medicine and application of the compound, the pharmaceutical composition and the medicine in preparation of antibacterial products. The seeking of a novel antibacterial target and the development of a novel chemical entity have important significance for solving the increasingly severe bacterial drug resistance problem at present, and the design of a compound entity acting on the FtsZ target is expected to be developed to obtain an antibacterial drug which has no influence on a host. The invention provides a 9-aralkyl-10-methylacridine quaternary ammonium salt derivative and a preparation method thereof, and the compound has significant bactericidal and/or bacteriostatic activity on gram-positive bacteria, has a good effect of inhibiting bacterial division protein FtsZ, and can be used for preparing antibacterial products.
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- Tert-Butyl Bromide-Promoted Intramolecular Cyclization of 2-Arylamino Phenyl Ketones and Its Combination with Cu-Catalyzed C-N Coupling: Synthesis of Acridines at Room Temperature
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Herein, a facile intramolecular cyclization of 2-arylamino phenyl ketones is established to supersede the traditional high-temperature, strongly acidic conditions and achieve 9-substituted acridines, by virtue of the combination of 2,2,2-trifluoroethanol and tert-butyl bromide. This protocol can be merged well with the preceding Cu-catalyzed intermolecular Chan-Evans-Lam cross-coupling reactions, therefore enabling pot-economic modular synthesis of 9-substituted acridines from readily available 2-amino phenyl ketones and aryl boronic acids at room temperature.
- Cao, Zifeng,Zhu, Yuan,Li, Xiaoman,He, Yang,Zhang, Jinli,Xu, Liang,Wei, Yu
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p. 10167 - 10174
(2020/09/03)
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- A Direct S0→Tn Transition in the Photoreaction of Heavy-Atom-Containing Molecules
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According to the Grotthuss–Draper law, light must be absorbed by a substrate to initiate a photoreaction. There have been several reports, however, on the promotion of photoreactions using hypervalent iodine during irradiation with light from a non-absorbing region. This contradiction gave rise to a mystery regarding photoreactions involving hypervalent iodine. We demonstrated that the photoactivation of hypervalent iodine with light from the apparently non-absorbing region proceeds via a direct S0→Tn transition, which has been considered a forbidden process. Spectroscopic, computational, and synthetic experimental results support this conclusion. Moreover, the photoactivation mode could be extended to monovalent iodine and bromine, as well as bismuth(III)-containing molecules, providing new possibilities for studying photoreactions that involve heavy-atom-containing molecules.
- Kuribara, Takahito,Matsumoto, Koki,Muranaka, Atsuya,Nagasawa, Sho,Nakajima, Masaya,Nemoto, Tetsuhiro,Uchiyama, Masanobu
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p. 6847 - 6852
(2020/03/23)
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- Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water
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A novel palladium-catalyzed protocol for the synthesis of 9-arylacridines via tandem reaction of 2-(arylamino)benzonitrile with arylboronic acids in water has been developed with good functional group tolerance. The present synthetic route could be readily scaled up to gram quantity without difficulty. This methodology was further extended to the synthesis of a 4′-OH derivative, which showed estrogenic biological activity. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular Friedel-Crafts acylation and dehydration to acridines.
- Ye, Xuanzeng,Xu, Beihang,Sun, Jiani,Dai, Ling,Shao, Yinlin,Zhang, Yetong,Chen, Jiuxi
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p. 13004 - 13014
(2020/11/23)
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- Aryl acridine derivative synthesized by palladium catalysis and preparation method thereof (by machine translation)
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When the reaction is carried out, the reaction temperature of the catalyst is very moderate, the reaction 2 - (temperature) of the catalyst is very moderate, the reaction; time of the, catalyst is, very moderate, and the reaction, is carried out at a reaction . temperature ranging from the reaction, time of the; reaction to the, solvent, 90 - 110 °C, 20 - 25, 94%. (by machine translation)
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Paragraph 0030-0035
(2020/02/14)
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- Preparation method of 9-phenyl acridine compound (by machine translation)
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The preparation method comprises the following 9 - steps: under the action 1 of a palladium catalyst, reacting the halogenated acridine compound of the formula I with 2 the phenylboronic acid or derivative thereof in a solvent under the action of a palladium catalyst 20 - 80 °C 3 9 . The halogen atom in the first X alkyl R group is 1 - 18 at least one halogen atom, and the alkyl group second is an alkyl group, an alkenyl group, an alkynyl group or a halogen atom. By adopting the method disclosed by the invention, the reaction 97% conversion rate is equal to or higher, the finished 99% product content after being subjected to post-treatment is higher than or equal to, and the process can meet the requirements of industrial production. (by machine translation)
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Paragraph 0030; 0031
(2019/11/21)
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- Method for preparing acridine derivative
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The invention relates to a method for preparing an acridine derivative, and specifically relates to a method for preparing the acridine derivative from an organic azide compound and a benzene compoundunder the action of an acid. According to the method disclosed by the invention, no transition metal catalyst is used, and the acridine derivative with an anthracene structure is obtained from a simple and easily-available raw material through simple operation steps.
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Paragraph 0014-0017; 0019
(2019/07/16)
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- Synthesis of Acridines from o-Aminoaryl Ketones and Arylboronic Acids by Copper Trifluoroacetate-Mediated Relay Reactions
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An efficient and practical method for the synthesis of medicinally important acridines from readily available o-aminoaryl ketones and arylboronic acids was developed using copper(II)-mediated relay reactions that involve intermolecular Chan-Lam cross-coupling and subsequent intramolecular Friedel-Crafts-type reactions. A sole promoter, i.e., Cu(OTf)2, was used; therefore, strongly acidic and basic conditions, nonreadily available or expensive substrates, additives, and noble-metal catalysts were not needed.
- Wu, Hao,Zhang, Zhiguo,Ma, Nana,Liu, Qingfeng,Liu, Tongxin,Zhang, Guisheng
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p. 12880 - 12886
(2018/10/09)
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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 0115-0118
(2018/05/16)
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- Synthesis of Substituted Acridines through a Palladium-Catalyzed Condensation/Cyclization/Tautomerization Sequence
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Herein, we report an efficient strategy for the synthesis of 9-aryl-substituted acridines from cyclohexanones and 2-aminobenzophenones in the presence of a palladium catalyst. Molecular oxygen is applied as a green oxidant. Various cyclohexanones acted as the aryl source to construct the nitrogen-containing heterocycles through a condensation/cyclization/tautomerization sequence.
- Chen, Xiangui,Xie, Yanjun,Li, Cheng,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 577 - 581
(2017/02/05)
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- Palladium-Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2-Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant
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A facile oxidative annulation of cyclohexanones and 2-aminophenyl ketones that uses molecular oxygen as the sole oxidant is described. The reaction provides a direct approach to acridines, a structural motif for a large number of fluorescent sensors, functional materials, ligands, and pharmaceuticals. In the presence of a palladium catalyst, high regioselectivity is observed when using non-symmetric 3-substituted cyclohexanones. With the use of oxygen as the terminal redox moderator, the electron gap of the global redox condensation process is filled and the reaction efficiency is significantly promoted. This protocol possesses many advantages such as using non-hazardous oxidant and readily available starting materials, high regioselectivity, and water as the only by-product. (Figure presented.).
- Mu, Wan-Lu,Wang, Meirong,Li, Hui-Jing,Huang, Deng-Ming,Zhang, Yi-Yun,Li, Chao-Yi,Liu, Ying,Wu, Yan-Chao
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supporting information
p. 4250 - 4257
(2017/12/15)
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- A magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle: An efficient and recyclable solid molecular catalyst for Suzuki-Miyaura cross-coupling of 9-chloroacridine
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A robust magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle has been readily synthesized by directly anchoring the structural defined acenaphthoimidazolylidene palladacycle with a long tail on magnetic nanoparticles (MNPs), and functioned as a solid molecular catalyst and exhibited extremely high catalytic activity towards the challenging Suzuki-Miyaura cross-coupling reactions between less-studied heterocyclic 9-chloroacridine and diverse boronic acids. Remarkably, the catalyst could be used 5 times without obvious loss of activity highlighting the efficiency of our strategy of immobilization of previledged catalysts.
- Deng, Qinyue,Shen, Yajing,Zhu, Haibo,Tu, Tao
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supporting information
p. 13063 - 13066
(2017/12/15)
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- Lattice energetics and thermochemistry of acridine derivatives and substituted acridinium trifluoromethanesulphonates
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The enthalpies and temperatures of melting of eight 9-substituted acridines (alkyl, aryl or alkoxy) (I) and six their 10-methylated-acridinium trifluoromethanesulphonate (II) derivatives were measured by DSC. The enthalpies and temperatures of volatilisation of the first group of compounds were also determined by DSC or obtained by fitting TG curves to the Clausius–Clapeyron relationship. By combining the enthalpies of formation of gaseous acridines or 10-methylacridinium trifluoromethanesulphonate ions, obtained by the DFT method, and the corresponding enthalpies of sublimation and/or crystal lattice enthalpies, the enthalpies of formation of the compounds in the solid phase were predicted. For compounds whose crystal structures are known, experimental enthalpies of sublimation correspond reasonably well to crystal lattice enthalpies predicted theoretically as the sum of electrostatic, dispersive and repulsive interactions. Analysis of crystal lattice enthalpy contributions indicates that dispersive interactions between molecules always predominate in the case of acridine derivatives, whilst the crystal lattices of their quaternary salts are stabilised by electrostatic interactions between ions. Only in the case of 9-bromomethylacridine derivative, which crystallises in the monohydrated form, electrostatic contribution to the crystal lattice energy is significantly higher than in the other investigated acridines.
- Zadykowicz, Beata,Storoniak, Piotr
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p. 1613 - 1624
(2017/08/16)
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- Preparation method of acridine compound
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The invention relates to a preparation method of an acridine compound. The structural formula of the prepared acridine compound is shown in the specification, wherein R1, R2 and R3 are selected from hydrogen atoms, alkyl, aryl, halogens, alkoxy, aryloxy, trifluoromethyl and the like. A dehydrogenation method comprises the steps that o-amino benzophenone and cyclohexanone serve as the reaction raw materials, methylbenzene serves as solvent, a reaction is conducted for 8 h at 150 DEG C under acid catalysis, and after the reaction is completed, a quinoline compound is obtained through concentration and column chromatography separation; the quinoline compound is reacted for 6 h on the condition that palladium trifluoroacetate and 1,10-phenanthroline hydrate serve as catalysts, NMP serves as solvent, O2 atmosphere exists, and the temperature is 100 DEG C, extraction, concentration and column chromatography purification are conducted, and the acridine compound is obtained. The yield ranges from 60 percent to 80 percent. According to the preparation method of the acridine compound, the o-amino benzophenone and the cyclohexanone serve as substrates, the quinoline compound is obtained through a Friedlander synthesis method, and an acridine derivative is obtained through a palladium catalysis and hydrogen transfer method, so that the preparation method of the acridine compound has the advantages that the raw materials are stable and easy to obtain, the product selectivity is good, operation is easy, and the preparation method is suitable for industrial production.
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Paragraph 0005
(2016/10/17)
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- Tandem arylation/friedel-crafts reactions of o-acylanilines with diaryliodonium salts: A modular synthesis of acridine derivatives
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A modular method to synthesize acridine derivatives was developed with o-acylanilines and diaryliodonium salts. The reactions proceeded smoothly under Cu-catalyzed or metal-free reaction conditions at elevated temperature through tandem arylation/Friedel-Crafts reactions.
- Pang, Xinlong,Lou, Zhenbang,Li, Ming,Wen, Lirong,Chen, Chao
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supporting information
p. 3361 - 3369
(2015/05/20)
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- Unexpected cyclization of tritylamines promoted by copper salt through c-h and c-n bond cleavages to produce acridine derivatives
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Herein, we demonstrate that tritylamines undergo an unprecedented copper-mediated cyclization involving the cleavages of two C-H bonds and one C-N bond to give 9-arylacridine derivatives. This kind of acridines is of interest due to their biological properties and their unique optical and electro- and photochemical properties. Some of obtained acridine derivatives exhibit intense fluorescence in the solid state.
- Morioka, Ryosuke,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 12720 - 12724
(2015/03/30)
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- Regioselective C-H bond functionalizations of acridines using organozinc reagents
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Despite the recent advance in C-H bond functionalization chemistry, the C-H bonds in the acridine ring system, which is an important scaffold in medicinal and material science, have met with limited success, due, in part, to the lack of activated C-H bonds adjacent to the ring nitrogen atom. Herein, several protocols that can effect the regioselective arylation and alkylation of acridines at the C-4 and C-9 positions are described.
- Hyodo, Isao,Tobisu, Mamoru,Chatani, Naoto
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supporting information; experimental part
p. 308 - 310
(2012/01/05)
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- Synthesis of acridines by the [4 + 2] annulation of arynes and 2-aminoaryl ketones
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(Figure Presented) The reaction of 2-aminoaryl ketones and arynes generated by the treatment of various o-(trimethylsilyl)aryl triflates with CsF results in [4 + 2] annulation to afford substituted acridines in good yields.
- Rogness, Donald C.,Larock, Richard C.
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supporting information; experimental part
p. 2289 - 2295
(2010/07/02)
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- Carbon nanotube-acridine nanohybrids: Spectroscopic characterization of photoinduced electron transfer
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Single-walled carbon nanotubes (NT) were covalently functionalized with either 9-phenyl acridine (PhA) or 10-methyl-9-phenyl acridinium (PhMeA +). Absorption and fluorescence properties of acridine derivatives tethered to the nanotubes were studied in homogeneous dispersions. Exciplex emission was observed for NT functionalized with 9-phenylacridine. This phenomenon was attributed to an " intramolecular" interaction between excited phenyl acridine and carbon nanotubes. Interestingly, reverse photoinduced electron transfer from the nanotube to 10-methyl-9-phenylacridinium was detected for the NTPhMeA+ nanohybrid. This electron transfer led to a strong quenching of the acridinium fluorescence and to the formation of a metastable acridine radical. Evidence for the formation of this radical was obtained by ESR studies.
- Mackiewicz, Nicolas,Delaire, Jacques A.,Rutherford, A. William,Doris, Eric,Mioskowski, Charles
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experimental part
p. 3882 - 3888
(2009/12/25)
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- Direct regioselective phenylation of acridine derivatives by phenyllithium
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Acridine and acridine derivatives have been converted directly to phenyl derivatives regioselectively using phenyllithium.
- Dutta, Bishnupada,Kar, Gandhi K.,Ray, Jayanta K.
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p. 8641 - 8643
(2008/04/18)
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- Rapid synthesis of acridines using microwave
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Microwave irradiation for several minutes caused reaction of diarylamines with carboxylic acids in the presence of zinc chloride to give 9-substituted acridines in good yield.
- Koshima, Hideko,Kutsunai, Kosuke
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p. 1299 - 1302
(2007/10/03)
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- Structural studies on bioactive compounds. Part 33. Synthesis of 9- arylacridines by palladium-mediated couplings
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9-Halogenoacridines undergo Suzuki cross-coupling reactions with a range of arylboronic and thienyl-3-boronic acids to yield substituted 9- arylacridines and 9-(thien-3-yl)acridines.
- Palat, Karel,Stevens, Malcolm F. G.
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p. 136 - 137
(2007/10/03)
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- Thermal decomposition of tert-butyl o-(phenoxy)- and o-(anilino)-phenyliminoxyperacetates
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Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The iminyls show no disposition to give 7-membered cyclisation on the phenyl group. In some cases, products have been found that can be rationalised through a 1,6-spirocyclisation of the iminyl radicals followed by homolytic 1,5-migration of the phenyl group from the aminic to the iminic nitrogen: this seems to be the first instance of such a process. Evidence has been found for the formation of imines through hydrogen abstraction by the iminyls; with two o-phenoxy-substituted peresters these imines have been unexpectedly isolated. The reactions have also afforded significant - in some cases major - amounts of other products (acridine, quinazolinone and indole derivatives) presumably deriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone compound has been determined by X-ray crystallographic analysis.
- Calestani, Gianluca,Leardini, Rino,McNab, Hamish,Nanni, Daniele,Zanardi, Giuseppe
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p. 1813 - 1824
(2007/10/03)
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- Base-mediated reactions of ortho- and para-perfluoroalkylanilines
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The title chemistry involves regioselectively a benzylic position of the perfluoroalkyl group and provides an easy access to substituted quinolines and methanes.
- Strekowski, Lucjan,Lin, Shou-Yuan,Lee, Hyeran,Mason, J. Christian
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p. 4655 - 4658
(2007/10/03)
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- Synthesis of Substituted Dibenzoazepines via a Base-Mediated Ring Expansion
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Substituted dibenzoazepines 5 and 10 were synthesized in three steps by starting from acridine (6).The key step of the synthesis is a base-mediated ring expansion reaction of the mesylates 1. Key Words: Dibenzoazepines / Norcaradienes, intermediates in ring expansion reactions
- Groth, U.,Richter, L.,Schoellkopf, U.
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p. 199 - 202
(2007/10/02)
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- STUDIES ON ENAMIDES. PART 4 : PHOTOCHEMICAL INVESTIGATIONS OF N-AROYLDIPHENYLAMINES
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Photolysis of N-aroyldiphenylamines affords 9-arylacridines or phenanthridinone depending on the structure of the substrates.Additionally, carbazole and photomigrated products are also obtained.
- Datta, Indira,Das, Tapas Kumar,Ghosh, Somnath
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p. 6821 - 6830
(2007/10/02)
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- STUDIES ON ENAMIDES. PART-3 : A NOVEL PHOTOCHEMICAL SYNTHESIS OF 9-ARYLACRIDINES
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A unique synthesis of 9-arylacridines has been achieved by the photolysis of N-aroyldiphenylamines alongwith carbazole and photomigrated products.
- Datta, Indira,Das, Tapas Kumar,Ghosh, Somnath
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p. 4009 - 4012
(2007/10/02)
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- Polar Effects in Free-Radical Reactions. Rate Constants in Phenylation and New Methods of Selective Alkylation of Heteroaromatic Bases
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The rate constants for the addition of the phenyl radical to protonated and unprotonated 4-substituted pyridines have been determined by competition with chlorine abstraction from CCl4.The constants range from 2 * 105 to 6 * 106 M-1 s-1 depending on the substituent and on the degree of protonation.The phenyl radical shows a clear-cut nucleophilic character.On the basis of these rate constants, the use of phenyl radical from diazonium salt or benzoyl peroxide to generate alkyl radicals by iodine or hydrogen abstraction has been developed as a general procedure for the alkylation of heteroaromatic bases.This reaction is characterized by high yields and selectivities.
- Minisci, Francesco,Vismara, Elena,Fontana, Francesca,Morini, Giampiero,Serravalle, Marco,Giordano, Claudio
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p. 4411 - 4416
(2007/10/02)
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- Molecular Rearrangements. XXIV. Thermolysis of Phenylhydrazones
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Thermolysis of acetophenone phenylhydrazone by reflux in air for 24 h gives ammonia, benzonitrile, acetophenone, biphenyl, aniline, o- and p-toluidines, together with 7-methyl-3-phenylindole, while that of benzophenone phenylhydrazone gives ammonia, benzo
- Mahgoub, Safaa Abd El-Salam,Fahmy, Atiat Mohammed,Aly, Morsy Mohammed,Badr, Mahmoud Zaif Amin
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p. 1605 - 1606
(2007/10/02)
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- CONVERSIONS OF o-AMINOTRIPHENYLCARBINOL IN THE PRESENCE OF LEWIS ACIDS
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9-Phenylacridinium hexahaloantimonates were produced by the action of antimony pentahalides on o-aminotriphenylcarbinol.The presence of halides of carboxylic acids directs the reaction toward the formation of 4,4-diphenyl-1,2-dihydro-4H-3,1-benzoxazinium hexahaloantimonates.
- Kul'nevich, V. G.,Gromachevskaya, E. V.,Kosulina, T. P.
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p. 776 - 778
(2007/10/02)
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- Molecular rearrangements. Part XVI. Thermolysis and photolysis of N-benzyldiphenylamine and N-phenylacetyldiphenylamine
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Heating N-phenylacetyldiphenylamine in a sealed tube at 360 deg C gave rise to carbon monoxide, bibenzyl, toluene, stilbene, diphenylmethane, aniline, carbazole, N-benzylcarbazole, acridine, 9-phenylacridine, 4-aminotriphenylmethane, diphenylamine, p-benzyldiphenylamine, and o-aminodiphenylmethane.A similar result was also obtained on heating N-benzyldiphenylamine, with the exception of carbon monoxide.Such results in addition to those obtained from photolysis of N-phenylacetyldiphenylamine are interpreted in terms of a free-radical mechanism.
- Badr, M.Z.A.,Aly, M.M.,Fahmy, A.M.
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p. 1229 - 1232
(2007/10/02)
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