ArticleOrganic letters2026
Formal [1,5] Rearrangement of Cyclopropanone Hemiaminals: Synthesis of Tetrahydrobenzazepinone Derivatives.
Article in Organic letters, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
A convergent synthetic approach to the formation of tetrahydrobenzazepin-2-ones from 2-aminobenzaldehyde derivatives and cyclopropanone surrogates is reported. In this process, a stable hemiaminal intermediate spontaneously rearranges at room temperature upon generation of a remote iminium species, via a concerted and diastereoselective ring opening/homo-Mannich pathway occurring through a boat transition state. Such a formal [1,5] rearrangement of cyclopropanone hemiaminals is unprecedented and thus represents a novel strategy for the elaboration of seven-membered heterocyclic compounds.
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