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2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities

Abstract : 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.
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Submitted on : Wednesday, September 8, 2021 - 3:44:11 PM
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Sarah Zeghada, Ghenia Bentabed-Ababsa, Olivier Mongin, William Erb, Laurent Picot, et al.. 2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities. Tetrahedron, Elsevier, 2020, 76 (38), pp.131435. ⟨10.1016/j.tet.2020.131435⟩. ⟨hal-03302141⟩



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