{
  "abstract": "A novel class of azido-modified α , β -unsaturated Ugi adducts (enamides) has been explored as a versatile platform for post -Ugi transformations. While intramolecular azide-alkyne cycloadditions of Ugi-derived peptidomimetics have been extensively studied, the corresponding azide-alkene cycloadditions on similar scaffolds have remained unexplored. In this work, we report a systematic investigation of intramolecular azide-alkene cycloaddition involving activated enamide moieties derived from Ugi adducts. Enamides readily undergo catalyst-free intramolecular [3+2] cycloaddition under mild conditions to afford the previously unknown 3,3a,4-trisubstituted-3a,4-dihydro-3 H -imidazo[1,2-c][1,2,3]triazol-5(6 H )-one scaffold in high yields. This novel fused heterocyclic system was fully characterised and proved to be a highly versatile intermediate for divergent post -Ugi transformations. Fused dihydrotriazoles transformed into 3,5-dihydroimidazol-4-ones via an elimination of N 2 supplemented by acylamide migration. Additionally, base- or acid-mediated cascades enabled efficient one-pot access to aromatised 1,2,3-triazoles and open-chain triamides, respectively. In total, 4 generations of structural isomers and 2 other classes of compounds were involved in the work. The methodologies developed highlight the synthetic value of azido-modified enamides as divergent intermediates, providing rapid and controlled entry to structurally diverse nitrogen-rich heterocycles and peptidomimetics from simple Ugi adducts derived from α , β- unsaturated aldehydes.",
  "abstract_shown": true,
  "affiliations": [
    "Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky Avenue 60, Kharkiv, Ukraine, 61072",
    "Institute of Organic Chemistry National Academy of Sciences of Ukraine, Akademik Kukhar Street 5, Kyiv, 02660",
    "Education and Research Institute of Chemistry, V. N. Karazin Kharkiv National University, Svobody Square 4, Kharkiv, Ukraine, 61022",
    "Department of Organic Chemistry, Biochemistry, Paints and Coatings, National Technical University “Kharkiv Polytechnic Institute”, Kyrpychova Street 2, Kharkiv, Ukraine, 61002"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 6,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Vladyslav Vereshchak",
      "orcid": "0009-0007-2329-9411"
    },
    {
      "affs": [
        0
      ],
      "name": "Viacheslav Saraiev",
      "orcid": "0000-0002-2312-8774"
    },
    {
      "affs": [
        0
      ],
      "name": "Vladimir Musatov",
      "orcid": "0000-0002-7457-9460"
    },
    {
      "affs": [
        1
      ],
      "name": "Svitlana Shishkina",
      "orcid": "0000-0002-3946-1061"
    },
    {
      "affs": [
        0,
        2
      ],
      "name": "Valentyn Chebanov",
      "orcid": "0000-0001-7564-778X"
    },
    {
      "affs": [
        0,
        3
      ],
      "name": "Alexander Tsygankov",
      "orcid": "0000-0001-5298-8450"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/4q2m417a0dsb3.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15009125/v1",
  "fulltext_url": null,
  "id": "4q2m417a0dsb3",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009125/v1",
  "language": null,
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Multicomponent Synthesis of Heterocycles"
    ]
  ],
  "openalex": "W7213907437",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15009125/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-09-21",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/4q2m417a0dsb3.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:19Z",
      "native_id": "10.26434/chemrxiv.15009125",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009125/v2"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Multicomponent Synthesis of Heterocycles",
      "subfield": "organic"
    }
  ],
  "title": "The first approach to highly substituted dihydroimidazotriazolones and their controlled post-transformations",
  "title_text": "The first approach to highly substituted dihydroimidazotriazolones and their controlled post-transformations",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:21Z",
  "url": "https://research.draconitic.com/paper/4q2m417a0dsb3",
  "venue": "ChemRxiv",
  "versions": []
}