225-11-6Relevant articles and documents
FeCl3-Promoted ring size-dictating diversity-oriented synthesis (DOS) of N-heterocycles using: In situ -generated cyclic imines and enamines
Dhandabani, Ganesh Kumar,Mutra, Mohana Reddy,Wang, Jeh-Jeng
, p. 7542 - 7545 (2019)
The FeCl3-promoted ring size-controlled oxidative activation of o-alkynylanilines opens up a complementary appealing protocol for poly-N-heterocycle synthesis. When electron-poor π-alkyne iron species combine with cyclic enamines obtained from cyclohexanone and β-tetralone, they undergo a regioselective 6-exo-dig cyclization to afford the corresponding dibenzo[b,j][1,10]phenanthrolines and 12-benzoylated dihydrobenzo[a]acridine skeletons. Later, these acridine motifs become completely unsaturated due to dehydrogenative aromatization via the aza-allyl oxidation intermediate. We obtained all quaternary carbon centre pseudoindoxyls through the Mannich-type alkylation of 2,3-dihydro-1H-inden-1-one with cyclic ketimines generated from the in situ intramolecular nucleophilic cyclization of o-alkynylanilines.
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.
Facile synthesis of acridine derivatives by ZnCl2-promoted intramolecular cyclization of o -arylaminophenyl schiff bases
Su, Qing,Li, Pei,He, Mina,Wu, Qiaolin,Ye, Ling,Mu, Ying
supporting information, p. 18 - 21 (2014/01/23)
A concise and efficient method for the synthesis of a wide range of acridine derivatives and polycyclic aza-aromatic compounds from a ZnCl 2-promoted cyclization reaction of readily available o-arylaminophenyl Schiff base compounds under convenient conditions was developed. Reaction conditions and scope of the new method were examined in detail.
