A novel DMAP-catalyzed [4+3] spiroannulation
of pyrazolone-derived
Morita–Baylis–Hillman carbonates with N-(o-chloromethyl)aryl amides was developed. This
reaction led to the assembly of medicinally relevant pyrazolone and
azepine nuclei into a structurally new spirocyclic scaffold, and a
diverse array of spiro[pyrazolone-azepine] products were afforded
in good to excellent yields (up to 93%) with a wide substrate scope
(23 examples) under mild conditions. Moreover, a gram-scale reaction
and product transformations were conducted, which further increased
the diversity of products.
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