108694-48-0Relevant academic research and scientific papers
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.
Nickel-Catalyzed Transformations of 2,1-Benzisoxazoles with Organozinc Reagents
Baum, Jonathan S.,Condon, Michael E.,Shook, David A.
, p. 2983 - 2988 (2007/10/02)
A novel transformation of 2,1-benzisoxazoles (anthranils) involving nitrogen-oxygen bond rupture with concomitant nitrogen-carbon bond formation by reaction with aryl-, methyl, or 2-thienylzinc chlorides in the presence of nickel catalyst is described.The products of the reaction are o-(substituted-amino)benzaldehydes and benzophenones, precursors of a series of heterocyclic derivatives, including acridines, quinolones, and the novel 7-chloro-1,3-dihydro-1,5-diphenyl-2H-1,4-benzodiazepin-2-one (21)
