Abstract
A new multicomponent domino reaction of cyclic enaminones with
acenaphthylene-1,2-dione in an anhydride solvent has been established,
providing selective protocol to pentacyclic indoles with different
substituted patterns (up to 50 examples). Both substitutions on the
cyclic enaminone ring and reaction temperatures showed obvious impact on
the reaction pathways. For instance, selective allylic hydroxylation and
allylic esterification of in situ generated indoles depend on reaction
temperatures. With special substituents, the reactions underwent
dehydrogenation process to give access to different substituted fused
indoles with good to excellent yields. These reactions feature mild
conditions, convenient one-pot operation and short reaction times. The
purification of products only needs to be washed by 95% ethanol without
traditional chromatography and recrystallization, which characterizes
group assisted purification (GAP) chemistry. (C) 2016 Published by
Elsevier Ltd.
Original language | English |
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Pages (from-to) | 4867-4877 |
Journal | Tetrahedron |
State | Published - Aug 2016 |