A novel protocol for the construction of highly functionalized
indolizine derivatives, that is, 1H-pyrrolo[3,4-b]indolizine-1,3-diones (PIZDOs, 3) from 2-(pyridine-2-yl)acetates
and maleimides via a regioselective oxidative [3 + 2] annulation was
developed. The cascade oxidative reaction was enabled by heating a
mixture of the two substrates in the presence of Ag2CO3 as an oxidant and Cu(OAc)·H2O as a catalyst
in chlorobenzene. Consequently, a series of PIZDOs 3 were
synthesized with high regioselectivity in moderate yields. This protocol
can be used in the synthesis of functionalized PIZDOs via the one-pot
oxidative annulation reaction rather than through multistep reactions,
which is suitable for both combinatorial and parallel syntheses of
PIZDOs.