42970-52-5Relevant academic research and scientific papers
Solvent-free and transition metal catalyst-free synthesis of indolo[1,2-f]phenanthridine from 6-chlorophenanthridine
Ageshina, A. A.,Asachenko, A. F.,Drokin, E. A.,Lysenko, A. N.,Minaeva, L. I.,Nechaev, M. S.,Rzhevskiy, S. A.,Sterligov, G. K.,Topchiy, M. A.
, p. 479 - 483 (2022/05/02)
A new easily scalable synthesis of the important for materials chemistry indolo[1,2-f]phenanthridine from commercially available 6-chlorophenanthridine was developed. The suggested transition metal catalyst-free and solvent-free procedure is more ecologically friendly and cost efficient then the known methods. The yields of indolo[1,2-f]phenanthridine synthesized from 6-chlorophenanthridine in three steps were 20% and 26% if the cyclization was carried out solvent-free and in THF in the presence of lithium 2,2,6,6-tetramethylpiperidide, respectively.
Enantioselective Atropisomeric Anilides Synthesis via Cu-Catalyzed Intramolecular Adjacent C-N Coupling
Fan, Xiaozhong,Zhang, Xue,Li, Chunyu,Gu, Zhenhua
, p. 2286 - 2291 (2019/02/19)
Catalytically asymmetric synthesis of atropisomeric compounds is an important research area in organic synthesis. However, in comparison with C-C atropisomers, the atropisomers caused by the restricted rotation of C-N single bonds have been given less att
Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3H)-ones with Benzynes for Construction of Phenanthridinone Scaffolds
Thorat, Vijaykumar H.,Upadhyay, Nitinkumar Satyadev,Murakami, Masahiro,Cheng, Chien-Hong
supporting information, p. 284 - 289 (2017/12/26)
The synthesis of phenanthridinones via denitrogenative annulation of 1,2,3-benzotriazin-4-(3H)-ones with arynes catalysed by Ni(0)/dppm was successfully developed. A variety of phenanthridinones were prepared in good to excellent yields. Based on this method, nature product, N-methylcrinasidine, was synthesized. (Figure presented.).
Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C-H Amidation
Moon, Yonghoon,Jang, Eunyoung,Choi, Soyeon,Hong, Sungwoo
supporting information, p. 240 - 243 (2018/01/17)
A straightforward synthetic strategy to construct biologically relevant phenanthridinones and quinolinones was developed via visible-light-promoted direct oxidative C-H amidation. In this photocatalytic system, amidyl radicals can be generated by homolysis of the N-H bond of simple amide precursors via single-electron transfer under blue LED illumination, which leads to oxidative intramolecular C-H amidation. Moreover, an efficient synthetic strategy using a photocascade enabled facile assembly of quinolinone structures through a catalytic sequence involving triplet energy (ET) transfer-based E/Z olefin isomerization and subsequent photocatalytic generation of amidyl radical intermediates.
Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives
Hirata, Tomoaki,Takahashi, Isao,Suzuki, Yuya,Yoshida, Hiroaki,Hasegawa, Hiroshi,Kitagawa, Osamu
, p. 318 - 323 (2016/01/15)
N-C axially chiral phenanthridin-6-one derivatives bearing various ortho-substituted phenyl groups on the nitrogen atom were enantioselectively prepared through (R)-DTBM-SEGPHOS-Pd(OAc)2-catalyzed intramolecular Buchwald-Hartwig amination. The enantioselectivity strongly depended on solvents, bases, and reaction temperature as well as on the bulkiness of ortho-substituents.
Organic electroluminescent device
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Page/Page column 127, (2016/06/01)
The present invention relates to electronic devices, in particular organic electroluminescent devices, comprising compounds of the formula (1), to the corresponding compounds, and to a process for the preparation of these compounds.
Practical Synthesis of Phenanthridinones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to o-Chlorobenzamides
Liu, Hailong,Han, Weibiao,Li, Chun,Ma, Zhiyong,Li, Ruixiang,Zheng, Xueli,Fu, Haiyan,Chen, Hua
supporting information, p. 389 - 393 (2016/02/18)
A highly efficient construction of phenanthridinone derivatives from o-halobenzamides was developed by using a phosphine-free palladium catalyst in N,N-dimethylacetamide. The domino reaction proceeds through a sequential C-C and C-N bond-formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o-chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover, the success of a gram-scale reaction demonstrated that this operationally simple process is scalable.
Sterically Hindered N-Aryl-2(1H)-Quinolones and N-Aryl-6(5H)-Phenanthridinones: Separation of Enantiomers and Barriers to Racemization
Mintas, Mhaden,Mihaljevic, Vesna,Koller, Helmut,Schuster, Doris,Mannschreck, Albrecht
, p. 619 - 624 (2007/10/02)
The novel N-aryl-4-chloro-3-methyl-2(1H)-quinolones (1)-(4) have been synthesized by condensation of the appropriate diphenylamine with diethyl methylmalonate and subsequent chlorination of the resulting N-aryl-4-hydroxy-3-methyl-2(1H)-quinolones (7)-(10). 5-(1-Naphthyl)-6(5H)-phenanthridinone (5) has been synthesized by the Chapman rearrangement of the 6-(1-naphthoxy)phenanthridine (11).Separation of the enantiomers (M) and (P) of the quinolones (1)-(4) and phenanthridinones (5), (6) was achieved by liquid chromatography on triacetylcellulose.The barriers to partial rotation about the C-N bond in (1)-(6) were determined by thermal racemization of enantiomers and are compared with those of structurally related molecules.
