{
  "abstract": "Skeletal editing enables the remodeling of aromatic frameworks, but pyridine-to-aniline conversions can generate multiple positional isomers, complicating analogue synthesis. Here we report an ipso-selective strategy that separates regiochemical control from diversification of the aniline nitrogen. Pyridines are converted through dearomatization and cycloaddition into stable, isolable bicyclic ketones, which undergo amine-induced condensation–fragmentation to afford anilines with the amino group positioned at the site corresponding to the original pyridine nitrogen. Both primary and secondary amines participate, enabling divergent synthesis from a common intermediate. Notably, regioisomeric intermediates derived from a 3-substituted pyridine converge to a single aniline product. The method also enables preparation of multiple analogues from a tropicamide-derived scaffold, illustrating the potential of this modular approach for medicinal-chemistry scaffold diversification.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry",
    "University of British Columbia"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 2,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Benjamin R. Boswell"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Corey R. J. Stephenson",
      "orcid": "0000-0002-2443-5514"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/19r8v8rvt0c93.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010949/v1",
  "fulltext_url": null,
  "id": "19r8v8rvt0c93",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010949/v1",
  "language": null,
  "licence": "CC-BY-NC",
  "licence_label": "CC BY-NC",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by-nc/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Advanced Synthetic Organic Chemistry"
    ]
  ],
  "openalex": "W7223378042",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010949/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-23",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/19r8v8rvt0c93.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:26Z",
      "native_id": "10.26434/chemrxiv.15010949",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010949/v2"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Advanced Synthetic Organic Chemistry",
      "subfield": "organic"
    }
  ],
  "title": "Ipso-selective pyridine-to-aniline editing through amine-induced fragmentation",
  "title_text": "Ipso-selective pyridine-to-aniline editing through amine-induced fragmentation",
  "type": "preprint",
  "updated_at": "2026-11-08T00:20:56Z",
  "url": "https://research.draconitic.com/paper/19r8v8rvt0c93",
  "venue": "ChemRxiv",
  "versions": []
}