An alkyl intercepted Meyer–Schuster
rearrangement reaction
with α,β-unsaturated ketones as the electrophiles was
first investigated, which provided a facile method to construct 2-methylene-pentane-1,5-diones.
Then the in situ generated 2-methylene-pentane-1,5-diones underwent
a Michael addition to give diverse 2-malononitrile methyl substituted
pentane-1,5-diones in a one-pot fashion. This transformation was reliable
on a gram scale. The high yield, convenient experimental operation,
and 100% atom economy made it a valuable method for the construction
of 1,2,3,5-tetrasubstituted pentane-1,5-dione derivatives.