Publication: Heterocyclizations at the Isocyanide Carbon: Mechanistic Insights into the 2-Isocyanoaniline to Benzimidazole Conversion
Authors
Alajarín Cerón, Mateo ; Marín Luna, Marta
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Publisher
American Chemical Society
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DOI
https://doi.org/10.1021/acs.joc.5c02202
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info:eu-repo/semantics/article
Description
Abstract
Benzo-fused heteroazacycles can form through spontaneous cyclizations of phenylisocyanides bearing some electron donor substituents at the ortho position. Although such reactions have been known since the 1970s, a clear mechanistic understanding of these transformations remains absent. Here, we disclose a detailed computational analysis aimed at elucidating the more plausible mechanism for one of these cyclizations, the o-isocyanoaniline to benzimidazole conversion. Our results show that a transient 1,4-diazabutatriene could play a key role in this cyclization by enabling a reaction pathway of lower barrier than the unimolecular concerted process.
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Citation
J. Org. Chem. 2026, 91, 4, 1837–1841
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