چكيده فارسي :
Since the discovery of C-H olefination of benzene by Fujiwara at 1967 [1] numerous
catalytic versions of this transformation have been developed. The vast majority of these
catalytic protocols proceed under ―ligandless‖ conditions (with PdII salts such as Pd(OAc)2 as
catalysts) and use oxidants such as peroxides, peroxyesters, dioxygen, polyoxometalates, CuII,
or AgI to achieve catalytic turnover [2]. Glycogen synthase kinase-3β (GSK-3βa) is
responsible for many important biological activities, such as Wnt and Hedgehog signaling
pathways, stem-cell renewal, meiosis steps, cellular differentiation, apoptotic mechanisms,
circadian rhythm, gene transcription as well as insulin action [3].Thus, the development of
GSK-3βinhibitors has been regarded as a potential therapeutic approachfor these related
diseases. Zou et al. found that benzo[e]isoindole-1,3-diones are of most powerful GSK-
3βinhibitors [4]. However, the traditional synthesis pathways of benzo[e]isoindole-1,3-diones,
are very complex, for example including sequential steps such as diazotization, low-yield
benzyne formation, Diels-Alder reaction, amidation of esters, cyclization via ortholithiation
and cabonization, oxidation of hemiaminal to amide and harsh dealkylation.Herein, we report
a direct method to the synthesis of benzo[e]isoindole-1,3-dione derivatives via tandem
oxidative coupling reactions of readily available raw materials.
