206645-70-7Relevant academic research and scientific papers
Synthesis of xanthones, thioxanthones and Acridones by a metal-free photocatalytic oxidation using visible light and molecular oxygen
Chinchilla, Rafael,Torregrosa-Chinillach, Alejandro
, (2021)
9H-Xanthenes, 9H-thioxanthenes and 9,10-dihydroacridines can be easily oxidized to the corresponding xanthones, thioxanthones and acridones, respectively, by a simple photo-oxidation procedure carried out using molecular oxygen as oxidant under the irradiation of visible blue light and in the presence of riboflavin tetraacetate as a metal-free photocatalyst. The obtained yields are high or quantitative.
N-Substitution of acridone with electron-donating groups: Crystal packing, intramolecular charge transfer and tuneable aggregation induced emission
Liu, Renfei,Zhang, Gang,Zhu, Guanxing
, p. 7092 - 7098 (2020)
Acridone derivatives with electron-rich triphenylamine functionalized at the amino position were synthesized and their properties were experimentally and computationally investigated. The single crystal structure analysis revealed that the π-π interaction of acridone and the formation of hydrogen bonds of carbonyl and the hydrogen atoms of the pending phenyl ring were crucial in the determination of molecular packing in the crystalline state. An intramolecular charge transfer (ICT) process was observed between acridone and triphenylamine even with reduced conjugation by the nitrogen atom of acridone. Tuneable aggregation induced emissions with blue and green fluorescence were found due to the different aggregation state and particle size, which varied according to the water content in THF. Furthermore, the size of the spacer between acridone and the appended amine was also important in adjusting the property of aggregation induced emission or aggregation caused quenching in the solid state.
2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities
Bentabed-Ababsa, Ghenia,Dorcet, Vincent,Erb, William,Mongin, Florence,Mongin, Olivier,Picot, Laurent,Roisnel, Thierry,Thiéry, Valérie,Zeghada, Sarah
, (2020/08/19)
By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse to a lithium-zinc base and converted to the corresponding 4-iodo derivative, which was involved in copper-catalyzed couplings with pyrrolidinone and pyrazole. Finally, addition of pyrazole, indole and carbazole onto the 9 position of bare acridine was improved. While moderate biological activity was noticed in melanoma cells growth inhibition, the newly prepared compounds feature interesting photophysical properties which were evaluated in a preliminary study.
Copper-catalyzed synthesis of N-aryl acridones from 2-amino benzophenones and aryl boronic acids via sequential double oxidative C–N coupling
He, Yang,Xu, Liang,Zhang, Jinli,Wei, Yu
, (2019/12/27)
Pot-economic synthesis of N-aryl acridones was performed with 2-aminobenzophenones and aryl boronic acids as starting materials. Cu-catalyzed chelation-assisted oxidative C–N cross-coupling reactions were well merged with the following intra-molecular oxidative dehydrogenative C–H amination reactions under an air atmosphere. The use of reagent capsules can further resolve the compatibility problem of reagents and simplify the operational process, providing a more straightforward access to the target products.
Mechanochromism, Twisted/Folded Structure Determination, and Derivatization of (N-Phenylfluorenylidene)acridane
Matsuo, Yutaka,Wang, Ya,Ueno, Hiroshi,Nakagawa, Takafumi,Okada, Hiroshi
supporting information, p. 8762 - 8767 (2019/05/29)
(N-Phenylfluorenylidene)acridane (Ph-FA) compounds with electron-withdrawing and -donating substituents (H, MeO, Ph, NO2, Br, F) at the para position of the phenyl group were successfully synthesized by Barton–Kellogg reactions of N-aryl thioacridones and diazofluorene. By using the substituent on the nitrogen atom to alter the electronic properties, both the folded and twisted conformers of p-NO2-C6H4-FA could be crystallographically characterized, which enabled the charge transfer from the electron-donating acridane moiety to the electron-accepting fluorenylidene moiety to be understood. Ground-state mechanochromism, thermochromism, vapochromism, and proton-induced chromism were demonstrated between the folded and twisted conformations of the conformers. Protonation and chemical oxidation of Ph-FA gave two stable acridinium compounds, namely, the fluorenylacridinium and acridinium radical cations. The present study will contribute to the development of functional dyes and organic semiconductors.
Synthesis of Acridones by Palladium-Catalyzed Buchwald-Hartwig Amination
Janke, Julia,Villinger, Alexander,Ehlers, Peter,Langer, Peter
supporting information, p. 817 - 820 (2019/04/25)
The Buchwald-Hartwig amination allows an efficient and convenient synthesis of biologically and pharmaceutically important acridones by formation of a six-membered ring. With the described method, a number of derivatives have been synthesized in up to 95% yield by using a variety of anilines as well as benzylic and aliphatic amines.
Organic compound with tetrahedral-like geometry
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Page/Page column 50; 51, (2018/03/25)
An organic compound with a tetrahedral-like geometry is disclosed. The organic compound has a structure represented by formula (I): wherein A1 to A4 each independently represent a 5-membered or 6-membered unsaturated ring; B1 represents direct bonding, —C—, —O—, —N—, —S— or —C═C—; m is 0 or 1; each of Ra's is independently hydrogen, fluorine, oxygen, substituted or unsubstituted C1-C12 alkyl or substituted or unsubstituted C6-C12 aryl; and n is an integer of 0 to 2.
Organic compound having tetrahedron-like configuration
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Paragraph 0171; 0173; 0174, (2018/07/07)
The present invention relates to an organic compound having a tetrahedron-like configuration, wherein the organic compound has a structure represented by the following general formula (I) defined in the specification, A1-A4 are respectively and independently an unsaturated five-membered ring or an unsaturated six-membered ring, B is a direct bond , -C, -O-, -N-, -S-, or -C=C-, m is 0 or 1, Ris hydrogen, fluorine, substituted or unsubstituted C1-C12 alkyl, or substituted or unsubstituted C6-C12 aryl, and n is an integer of 0-2. The organic compound of the present invention has excellentphotoelectric property.
Copper-catalyzed intramolecular oxidative C-H functionalization and C-N formation of 2-aminobenzophenones: Unusual pseudo-1,2-shift of the substituent on the aryl ring
Huang, Pang-Chi,Parthasarathy, Kanniyappan,Cheng, Chien-Hong
supporting information, p. 460 - 464 (2013/02/23)
A good move: A copper-catalyzed intramolecular oxidative C-H functionalization of 2-aminobenzophenone affords two regioisomeric acridones (see scheme). The reaction involves an unusual pseudo-1,2-migration of R 2 group(s) on the arene ring (bpy=2,2-bipyridine, DMAc=dimethylacetimide). Copyright
Thermal and chemiluminescent property of dioxetanes having an N-arylacridane structure
Imanishi, Takeshi,Ueda, Yohko,Tainaka, Ryoh,Kuni, Naoto,Minagawa, Masatoshi,Hoshino, Nobuhiro,Miyashita, Kazuyuki
, p. 829 - 838 (2007/10/03)
Novel dioxetanes having an N-arylacridane structure were synthesized. Studies on thermal stability and chemiluminescent property of these . compounds showed that the aryl group cannot stabilize the dioxetane structure so much but can trigger the chemiluminescence by formation of the phenoxy anion.
