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Heterocyclizations at the Isocyanide Carbon: Mechanistic Insights into the 2-Isocyanoaniline to Benzimidazole Conversion

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dc.contributor.authorAlajarín Cerón, Mateo
dc.contributor.authorMarín Luna, Marta
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2026-02-25T16:54:49Z
dc.date.available2026-02-25T16:54:49Z
dc.date.copyright© 2026 American Chemical Society after peer review and technical editing by the publisher
dc.date.issued2026-01-15
dc.description.abstractBenzo-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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dc.format.extent5
dc.identifier.citationJ. Org. Chem. 2026, 91, 4, 1837–1841
dc.identifier.doihttps://doi.org/10.1021/acs.joc.5c02202
dc.identifier.eissn1520-6904
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10201/213701
dc.languageeng
dc.publisherAmerican Chemical Society
dc.relationThis work was supported by PID2023-149097NB-I00, funded by MICIU/AEI/10.13039/501100011033 and ERDF/EU, and Project 21907/PI/22, funded by Fundacion Seneca-CARM.
dc.relation.publisherversionhttps://pubs.acs.org/doi/full/10.1021/acs.joc.5c02202
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International*
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectHeterocyclization
dc.subject1,4 Diazabutatriene
dc.subjectBenzimidazole
dc.subjectIsocyanide
dc.subject.odsNo relacionado con ningún objetivo de desarrollo sostenible
dc.titleHeterocyclizations at the Isocyanide Carbon: Mechanistic Insights into the 2-Isocyanoaniline to Benzimidazole Conversion
dc.typeinfo:eu-repo/semantics/article
dc.type.versioninfo:eu-repo/semantics/acceptedVersion
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relation.isAuthorOfPublicationa85354de-54fb-479f-9c99-86fc40dd9268
relation.isAuthorOfPublicationf93f811a-df96-4248-8396-9ddd85b349b0
relation.isAuthorOfPublication.latestForDiscoverya85354de-54fb-479f-9c99-86fc40dd9268
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