Synthesis of 5‐Seleno‐Substituted Spirocyclopenta[<i>b</i>]pyridine‐2,5‐dien‐4‐ones and Benzo[<i>h</i>]quinolines <i>via</i> Radical Cyclization of Arylethynylpyridines
A practical strategy for obtaining novel 5-seleno-substituted spirocyclopenta[b]pyridines-2,5-dien-4-ones and benzo[h]quinolines via radical cyclization is reported. The synthetic protocol explores the reaction between arylethynylpyridines and diorganyl diselenides in acetonitrile as solvent and Oxone® as oxidant at 82 °C. This easy-to-handle, eco-friendly metal-free approach was carried out under an open atmosphere, affording functionalized organoselenium compounds in good to excellent yields. Control experiments and scale-up test were performed to demonstrate the efficiency of this methodology.
Authors
- Raquel G. Jacob (ORCID: https://orcid.org/0000-0001-9603-3795)
- Rafaela R. S. A. Santos (ORCID: https://orcid.org/0000-0002-0566-862X)
- Ricardo H. Bartz (ORCID: https://orcid.org/0000-0003-4269-3389)
- Gelson Perin (ORCID: https://orcid.org/0000-0003-0359-0811)
- Márcio S. Silva (ORCID: https://orcid.org/0000-0002-7606-564X)
- Paola S. Hellwig (ORCID: https://orcid.org/0000-0002-6087-707X)
- Eder J. Lenardão (ORCID: https://orcid.org/0000-0001-7920-3289)
Institutions
- Universidade Federal de Pelotas (BR)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2024-09-19
- DOI
- https://doi.org/10.1002/asia.202400974
- Citations
- 4
- Primary Topic
- Organoselenium and organotellurium chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.40
Funders
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul
- Financiadora de Estudos e Projetos