2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities
作者:Sarah Zeghada、Ghenia Bentabed-Ababsa、Olivier Mongin、William Erb、Laurent Picot、Valérie Thiéry、Thierry Roisnel、Vincent Dorcet、Florence Mongin
DOI:10.1016/j.tet.2020.131435
日期:2020.9
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
从共同的底物2-氨基苯甲醛开始,制备了cr啶和a啶酮。前者是通过铜催化的N-芳基化反应,然后进行酸介导的环化反应而以高收率产生的,而后者是通过双重铜催化的N-芳基化,然后在相同反应条件下环化。此外,a啶通过依赖于锂锌碱进行去金属化并转化为相应的4-碘衍生物,其与吡咯烷酮和吡唑参与铜催化的偶联。最后,将吡唑,吲哚和咔唑添加到裸a啶的9位上得到改善。虽然在黑素瘤细胞生长抑制中注意到了适度的生物学活性,但新制备的化合物具有有趣的光物理性质,这些性质在初步研究中已进行了评估。