- 2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities
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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.
- Bentabed-Ababsa, Ghenia,Dorcet, Vincent,Erb, William,Mongin, Florence,Mongin, Olivier,Picot, Laurent,Roisnel, Thierry,Thiéry, Valérie,Zeghada, Sarah
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- Facile synthesis of acridine derivatives by ZnCl2-promoted intramolecular cyclization of o -arylaminophenyl schiff bases
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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.
- Su, Qing,Li, Pei,He, Mina,Wu, Qiaolin,Ye, Ling,Mu, Ying
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supporting information
p. 18 - 21
(2014/01/23)
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- Indium-catalyzed construction of polycyclic aromatic hydrocarbon skeletons via dehydration
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Polycyclic aromatic compounds can be synthesized from 2-benzylic- or 2-allylbenzaldehydes using a catalytic amount of In(III) or Re(I) complexes. By using this method, polycyclic aza-aromatic compounds can also be prepared efficiently. In these reactions, only water is formed as a side product.
- Kuninobu, Yoichiro,Tatsuzaki, Tomohiro,Matsuki, Takashi,Takai, Kazuhiko
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experimental part
p. 7005 - 7009
(2011/10/09)
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