65753-71-1Relevant articles and documents
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.
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
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.
