December 3, 2025

Switchable Synthesis of Fused Dihydrobenzofuran or Spiro Benzoisoxazole Derivatives Featuring a Migrated or Merged Directing Group

Puntos clave

Fused dihydrobenzofuran and spiro benzoisoxazole derivatives were generated with differing selectivity, demonstrating effective product tunability.
Using DCM resulted in C-H activation and [3 + 2] annulation, while DMSO with an oxidant led to [4 + 1] spiroannulation.
This method focuses on cascade reactions of N-phenoxyacetamide and diazo indandione, emphasizing diverse product formation.
The approach highlights moderate anticancer activity and broad substrate scope, presenting a potential for scalability and high atom economy.

Resumen

Generating different molecular scaffolds from the same starting materials is an attractive strategy for diversity-oriented synthesis. Presented herein is a switchable synthesis of dihydrobenzofuran-fused indanone or benzoisoxazole spiroindandione based on the cascade reactions of N-phenoxyacetamide with diazo indandione. The selectivity toward different products is expediently manipulated by tuning reaction conditions with the nature of the solvent as a key factor. When the reaction is carried out in DCM, the former is formed through C-H activation (CHA)-initiated 3 + 2 annulation along with acetamide group migration. When the reaction is carried out in DMSO in the presence of a stoichiometric amount of an external oxidant, on the other hand, the latter is generated through CHA-initiated 4 + 1 spiroannulation with directing group retention. In general, this novel protocol features easily tunable selectivity, simple substrates with a broad scope, valuable products with moderate anticancer activity, unique reaction pathways, high atom economy, and ready scalability.

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