ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024
Ring Transformation of Cyclopropenes to Benzo-Fused Five-Membered Oxa- and Aza-Heterocycles via a Formal [4+1] Cyclization.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
2 citing papers in PubMed.
- Enantioselective Cobalt(III)-Catalyzed [4 + 1] Annulation of Benzamides: Cyclopropenes as One-Carbon Synthons.Journal of the American Chemical Society · 2025Article
- Ring Transformation of Cyclopropenes to Benzo-Fused Five-Membered Oxa- and Aza-Heterocycles via a Formal [4+1] Cyclization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
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Authors and funding
11 authors.
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Abstract
In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo-fused five-membered oxa- and aza-heterocycles through a formal [4+1] cyclization and subsequent acid-catalyzed intramolecular O- to N- rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late-stage modification of complex molecules and in the synthesis of a potential PD-L1 gene down-regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)-mediated sequential C─H coupling/π-allylation/dynamically favorable O-attack route.
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