- Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids
-
An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.
- Huang, Yan-Xia,Huang, Zhuo-Jun,Jiang, Chun-Yong,Liang, Jing-Yi,Liang, Qiu-Ping,Shu, Bing,Xie, Hui,Zeng, Jun-Yi,Zhang, Shang-Shi,Zhou, Binhua
-
p. 8487 - 8491
(2021/10/20)
-
- N-substituted-3(10H)-acridones as visible-light photosensitizers for organic photoredox catalysis
-
N-Substituted-3(10H)-acridones have been established as visible-light organic photocatalyst. These photosensitizers are efficient for oxidative coupling reaction of N-aryl tetrahydroisoquinolines with various nucleophiles. Notably, N-methyl-3(10H)-acridon
- Chen, Kun,Cheng, Yong,Chang, Yongzhi,Li, Enqin,Xu, Qing-Long,Zhang, Can,Wen, Xiaoan,Sun, Hongbin
-
p. 483 - 489
(2017/12/26)
-
- Transition-Metal-Free Synthesis of Acridones via Base-Mediated Intramolecular Oxidative C?H Amination
-
Intramolecular oxidative C?H amination of 2-aminobenzophenones was achieved in the presence of potassium tert-butoxide and dimethyl sulfoxide. A series of functionalized acridones were prepared in moderate to excellent yields in a mild, efficient, and transition-metal-free manner. (Figure presented.).
- Wei, Wen-Tao,Sheng, Jian-Fei,Miao, Hui,Luo, Xiang,Song, Xian-Heng,Yan, Ming,Zou, Yong
-
supporting information
p. 2101 - 2106
(2018/06/14)
-
- 10-substituted acridine-3(10)-ketone compound, and preparation method and application thereof
-
The invention relates to a photosensitizer in photodynamic therapy, in particular to a 10-substituted acridine-3(10)-ketone compound shown in the formula I, a preparation method of the compound and application of the compound serving as the photosensitize
- -
-
-
- Acridone-benzimidazole ring-fused ligands: A new class of sensitizers of lanthanide luminescence via low-energy excitation
-
Two monotopic tridentate ligands, namely HLAB1 and HL AB2 have been synthesized which feature an acridone chromophore fused on a benzimidazolepyridine framework. They differ from each other by their connection points between a N-meth
- Deiters, Emmanuel,Gumy, Frederic,Buenzli, Jean-Claude G.
-
p. 2723 - 2734
(2010/08/21)
-
- Structure-activity relationships in the acronycine and benzo[b]acronycine series: Role of the pyran ring
-
In order to explore the structure-activity relationships in the acronycine series, simplified analogues of cis-1,2-diacetoxy-1,2-dihydroacronycine and cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1, under clinical trials) lacking the fused pyran ring, but possessing an acetoxymethyl leaving group at position 4 were prepared. These new analogues only displayed marginal antiproliferative activity compared to the parent compounds. The presence of the angularly fused dimethylpyran ring appears as an indispensable structural requirement to observe significant cytotoxic activity in this series.
- Do, Quyen,Thi Mai, Huong Doan,Gaslonde, Thomas,Pfeiffer, Bruno,Leonce, Stephane,Pierre, Alain,Michel, Sylvie,Tillequin, Francois,Dufat, Hanh
-
scheme or table
p. 2677 - 2687
(2009/04/11)
-
- An In-depth Study of the Azidobenzophenone-Anthranil-Acridone Transformation
-
The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts.Thus the conversion of 3-(p-tolyl)anthranil into an acridone gives a ratio of 2-and 3-methyl derivatives varying from 0.6:1 to 4.7:1 with changing temperature and solvent.In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction.The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted phenyl)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential -sigmatropic shifts. 3-Thienylanthranils gave related thienoquinolones on thermolysis; again the reaction were very sensitive to catalysis.Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.
- Hawkins, David G.,Meth-Cohn, Otto
-
p. 2077 - 2087
(2007/10/02)
-
- Coenzyme Models. 28. Facile Oxidation of Alcohols and Amines by 3-Hydroxy-N-methylacridinium Ion, a New NAD+ Model Compound
-
The title compound (Ac+OH) was synthesized for the purpose of developing a new NAD+ model compound which is capable of oxidizing alcohols and amines.The absorption spectrum of Ac+OH was similar to that of N-methylacridinium ion (Ac+) in the acidic pH region and to that of 5-deazaflavin in the basic pH region.The absorption spectrum of the reduced form was analogous to that of 3-aminophenol.The reduced form which was prepared by NaBH4 reduction was promptly reoxidized by molecular oxygen.With the aid of potassium tert-butoxide, Ac+OH oxidized benzyl alcoholand cyclohexanol to the corresponding aldehyde and ketone in almost quantitative yields.In contrast, Ac+ was totally useless as an oxidant under the same reaction conditions.Benzylamine was oxidized by Ac+ to benzaldehyde in low yields (11-24percent).On the other hand, the oxidation by Ac+OH occurred in good yields (82-88percent).When the reaction was carried out under an oxygen stream, the yield calculated on the basis of Ac+OH was enhanced up to 1800-2200percent.The results indicate that Ac+OH acts as an effective turnover oxidizing agent and that the 3-hydroxyl group plays a crucial role in the redox reactions occurring on the acridinium nucleus.This is the first example of the facile oxidation of alcohols and amines which mimics the catalytic behavior of NAD+ coenzyme.
- Shinkai, Seiji,Hamada, Hisatake,Kuroda, Hideo,Manabe, Osamu
-
p. 2333 - 2338
(2007/10/02)
-
- FACILE OXIDATION OF ALCOHOLS BY 3-HYDROXY-N-METHYLACRIDINIUM ION (A NEW NAD+ MODEL COMPOUND)
-
3-Hydroxy-N-methylacridinium iodide (Ac+OH) oxidized alcohols with the aid of potassium t-butoxide, whereas N-methylacridinium iodide (Ac+) could not oxidize alcohols under the same reaction conditions.The results indicate that the 3
- Shinkai, Seiji,Hamada, Hisatake,Kuroda, Hideo,Manabe, Osamu
-
p. 1235 - 1238
(2007/10/02)
-