70401-28-4Relevant academic research and scientific papers
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
Cao, Zifeng,Zhu, Yuan,Li, Xiaoman,He, Yang,Zhang, Jinli,Xu, Liang,Wei, Yu
, p. 10167 - 10174 (2020/09/03)
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.
Synthesis of Acridines from o-Aminoaryl Ketones and Arylboronic Acids by Copper Trifluoroacetate-Mediated Relay Reactions
Wu, Hao,Zhang, Zhiguo,Ma, Nana,Liu, Qingfeng,Liu, Tongxin,Zhang, Guisheng
, p. 12880 - 12886 (2018/10/09)
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.
Palladium-Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2-Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant
Mu, Wan-Lu,Wang, Meirong,Li, Hui-Jing,Huang, Deng-Ming,Zhang, Yi-Yun,Li, Chao-Yi,Liu, Ying,Wu, Yan-Chao
supporting information, p. 4250 - 4257 (2017/12/15)
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.).
Preparing method of substituted acridine derivatives
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Paragraph 0037-0039, (2017/02/09)
The invention discloses a method for preparing a multi-substituted acridine derivative with high efficiency and belongs to a chemical preparation technology. A structural formula of the multi-substituted acridine derivative is shown in a formula (I); the
Tandem arylation/friedel-crafts reactions of o-acylanilines with diaryliodonium salts: A modular synthesis of acridine derivatives
Pang, Xinlong,Lou, Zhenbang,Li, Ming,Wen, Lirong,Chen, Chao
supporting information, p. 3361 - 3369 (2015/05/20)
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.
Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade
Lian, Yajing,Hummel, Joshua R.,Bergman, Robert G.,Ellman, Jonathan A.
supporting information, p. 12548 - 12551 (2013/09/23)
We report formal [3 + 3] annulations of aromatic azides with aromatic imines and azobenzenes to give acridines and phenazines, respectively. These transformations proceed through a cascade process of Rh(III)-catalyzed amination followed by intramolecular electrophilic aromatic substitution and aromatization. Acridines can be directly prepared from aromatic aldehydes by in situ imine formation using catalytic benzylamine.
Auto-tandem catalysis: Synthesis of acridines by Pd-catalyzed C=C bond formation and C(sp2)-N cross-coupling
Huang, Zhongxing,Yang, Yang,Xiao, Qing,Zhang, Yan,Wang, Jianbo
, p. 6586 - 6593 (2013/01/15)
A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C-N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized acridine derivatives, which are generally difficult to synthesize by previously known methods.
Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: Preparation of carbazoles, indoles, dibenzazepines, and acridines
Tsvelikhovsky, Dmitry,Buchwald, Stephen L.
supporting information; experimental part, p. 14048 - 14051 (2011/01/04)
The Pd-catalyzed condensation of 2-bromostyrene and 2-chloroaniline derivatives yields stable diphenylamine intermediates, which are selectively converted to five-, six-, or seven-membered heteroaromatics (indoles, carbazoles, acridines, and dibenzazepines). The selectivity of these intramolecular transformations is uniquely ligand-controlled and offers efficient routes to four important classes of heterocycles from a common precursor.
Synthesis of 2-methylcarbamazepine, a new internal standard for chromatographic assays of carbamazepine (Tegretol)
Patton,Dudley
, p. 257 - 262,258,261 (2007/10/04)
The synthesis of 2-methyl-5H-dibenz[b,f]azepine-5-carboxamide (2-methylcarbamazepine, 2-MCBZ), a promising internal standard for chromatographic assays of the antiepileptic agent carbamazepine is described. N-(p-tolyl)anthranilic acid was utilized as a starting material for the synthesis of a key compound, 2,9-dimethylacridine, which was converted in two steps to 2-methyl-9-hydroxymethylacridan. The acridan, in the presence of polyphosphoric acid, was ring-expanded to form 2-methyl-5H-dibenz[b,f]azepine, this latter compound being converted by conventional reactions to its 5-carbamyl derivative, 2-MCBZ.
