Pyrrolo[2,1‐ <i>f</i> ][1,2,4]triazin‐4‐amine: Synthesis, <i>C</i> 7‐Functionalization, and NH <sub>2</sub> ‐Derivatization via Buchwald–Hartwig‐Type Coupling
An optimized gram‐scale synthetic route to pyrrolo[2,1‐ f ][1,2,4]triazin‐4‐amine is reported, affording an overall yield of 85%. Furthermore, regioselective C 7‐functionalization is achieved via both organometallic and direct strategies, whereas NH 2 ‐derivatization proceeds through Buchwald–Hartwig‐type coupling, providing derivatives in isolated yields ranging from 8% to >99%. These advancements enhance synthetic accessibility and facilitate efficient structural diversification of this significant N ‐heterocycle.
Authors
- Guillermo Vargas
- Vagner D. Pinho
- Juliana Alves dos Santos (ORCID: https://orcid.org/0000-0002-8636-4002)
- Taniris Cafiero Braga (ORCID: https://orcid.org/0000-0002-4032-0100)
- Vinícius Rodrigues Durães Pereira
- Giovanni W. Amarante (ORCID: https://orcid.org/0000-0003-1004-5395)
- Giuliano Cesar Clososki
- Jaime Alberto Rabi Nallar
Institutions
- Universidade Federal de Juiz de Fora (BR)
- Universidade de Ribeirão Preto (BR)
- Rede de Química e Tecnologia (PT)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2025-10-24
- DOI
- https://doi.org/10.1002/ejoc.202500512
- Primary Topic
- Synthesis and Reactivity of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa do Estado de Minas Gerais