225-51-4Relevant articles and documents
Copper-Catalyzed N,N-Diarylation of Amides for the Construction of 9,10-Dihydroacridine Structure and Applications in the Synthesis of Diverse Nitrogen-Embedded Polyacenes
Tan, Mei-Ling,Tong, Shuo,Hou, Sheng-Kai,You, Jingsong,Wang, Mei-Xiang
supporting information, p. 5417 - 5422 (2020/07/08)
We reported herein CuI/DMEDA catalyzed N,N-diarylation reaction of amides with various di(o-bromoaryl)methanes to produce diverse 9,10-dihydroacridine derivatives. The resulting 9,10-dihydroacridine derivatives were oxidized selectively under mild conditions to afford acridine, acridinone, and acridinium derivatives. The copper-catalyzed N,N-diarylation reaction coupled with oxidative aromatization reaction enabled the facile construction of nitrogen atom-embedded tetracenes and pentacenes of different ortho-fused patterns. The luminescence properties, especially the effect of fusion pattern on fluorescence emission of acquired N-polycenes, were also demonstrated.
Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole
Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
, p. 216 - 219 (2018/01/17)
A nitrogen-iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a nonsteroidal anti-inflammatory drug) were efficiently established through this protocol.
Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines
Shestakov, Aleksandr N.,Pankova, Alena S.,Kuznetsov, Mikhail A.
, p. 1103 - 1113 (2017/12/08)
[Figure not available: see fulltext.] Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]-acridines. Substituent at the triple bond governs a choice between transition metal or Br?nsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the o-aryl(phenylethynyl) fragment. PtCl2 efficiently catalyzes cyclization of 2-aryl-3-ethynylhetarenes.
