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Synthesis 2019; 51(11): 2293-2304
DOI: 10.1055/s-0037-1611747
DOI: 10.1055/s-0037-1611747
paper
Synthesis of 4-Organoselanyl-1H-pyrazoles: Oxone®-Mediated Electrophilic Cyclization of α,β-Alkynyl Hydrazones by Using Diorganyl Diselenides
The authors are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS) for financial support (Grant number: 17/2551-0000987-8). This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) (finance Code 001). CNPq is also acknowledged for fellowships to G.P., R.G.J., and E.J.L.Further Information
Publication History
Received: 17 December 2018
Accepted after revision: 05 February 2019
Publication Date:
14 March 2019 (online)
Abstract
A simple and efficient method for the synthesis of 4‑organoselanyl-1H-pyrazoles has been developed, taking place under metal- and halogen-free conditions. Electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone® in ethanol as solvent in an open-flask at 70 °C. These electrophilic selenium species were employed in the selenylation/cyclization of α,β-alkynyl hydrazones, giving the title compounds in moderate to excellent yields. The final species of selenium obtained from the reaction of diphenyl diselenide with Oxone® were characterized by 77Se NMR spectroscopy and high-resolution mass spectrometry (HRMS).
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611747.
- Supporting Information
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