65753-71-1Relevant academic research and scientific papers
Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids
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
supporting information, p. 8487 - 8491 (2021/10/20)
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.
Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from o-Aminoacetophenones and Arylboronic Acids
Wu, Hao,Zhang, Zhiguo,Liu, Qingfeng,Liu, Tongxin,Ma, Nana,Zhang, Guisheng
supporting information, p. 2897 - 2901 (2018/05/29)
The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3)-H amination, and C(sp2)-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields.
Preparation and characterization of thermochemiluminescent acridine-containing 1,2-dioxetanes as promising ultrasensitive labels in bioanalysis
Di Fusco, Massimo,Quintavalla, Arianna,Trombini, Claudio,Lombardo, Marco,Roda, Aldo,Guardigli, Massimo,Mirasoli, Mara
, p. 11238 - 11246 (2013/12/04)
Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.
Copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(Arylamino)aryl]ethanones leading to acridone derivatives
Yu, Jipan,Yang, Haijun,Jiang, Yuyang,Fu, Hua
, p. 4271 - 4277 (2013/04/24)
Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as the oxidant, and the corresponding acridones with various functional groups were obtained in moderate to good yields. Acridone synthesis: Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond (see scheme). The protocol uses inexpensive Cu(O 2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as oxidant. The corresponding acridones with various functional groups were obtained in moderate to good yields. Copyright
Copper-catalyzed C-C bond cleavage and intramolecular cyclization: An approach toward acridones
Zhou, Wang,Yang, Youqing,Liu, Yong,Deng, Guo-Jun
supporting information, p. 76 - 80 (2013/02/23)
A copper-catalyzed approach for the synthesis of acridones via C-C bond cleavage and intramolecular cyclization using air as the oxidant under neutral conditions is described. This transformation offers an alternative method to prepare medicinally important acridones and a new strategy for C-C bond cleavage.
Directed Ortho Metalation of N,N-Diethylbenzamides. Silicon Protection of Ortho Sites and the o-Methyl Group
Mills, Robert J.,Taylor, Nicholas J.,Snieckus, Victor
, p. 4372 - 4385 (2007/10/02)
New general methodology of value in aromatic chemistry based on silicon protection of preferred ortho metalation sites in benzamides and o-methyl groups in o-toluamides (1, 2, Scheme I) is described.According to these methodologies, routes (Scheme II and V) to 1,2,5-, 1,2,4,5-, and 1,2,3-substituted aromatics with a variety of functionalities and oxidation states have been developed (Tables I and II).These tactics are used for the synthesis of difficult to access halo (10a-b, Scheme III) and methyl (21,25, Scheme VI) heterocycles.Ipso bromodesilylation reactions with bromine lead regiospecifically to o-bromobenzamides (12a,c, 14, Scheme IV).Walk-around-the-ring metalation processes provide highly substituted aromatics 27, 28, 29, and 30 (Scheme VII); the X-ray structure of the hexasubstituted derivative 30 shows a significant puckering of the aromatic ring.Cesium fluoride induced carbodesilylation of o-silylbenzamides with benzaldehyde affords, after TsOH cyclization, phthalides (31a-c, Scheme VIII) and constitutes a neutral alternative to the directed ortho metalation approach. α- and α,α-silylated o-toluamides are used in fluoride-mediated carbodesilylation (34a,d, Scheme IX) and desilylative Peterson olefination (35, Scheme X) procedures, respectively.The utility of α-silylated o-toluamide for the synthesis of a tetralin (38, Scheme XI) via an o-quinodimethane species is given.
