N-Substituted 7-aminocoumarins can be synthesized from
readily
available 7-hydroxycoumarins via alkylation with α-bromoacetamides
and subsequent tandem O → N Smiles rearrangement–amide
hydrolysis. The key rearrangement sequence proceeds under mild conditions
to provide convenient access to various
N
-alkyl and
N
-aryl products in moderate to high yields. The process
is operationally simple, inexpensive, transition-metal-free, and can
be telescoped into a one-pot process.
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