A Selenium-Based Ionic Liquid as a Recyclable Solvent for the Catalyst-Free Synthesis of 3-Selenylindoles
Abstract
:1. Introduction
2. Results and Discussion
entry | ionic liquid | X | time (h) | yield (%) b |
---|---|---|---|---|
1 | [bmim][SeO2(OCH3)] | Cl | 3 | 78 |
2 | [pbeSe][BF4] | Cl | 3 | 39c |
3 | [bmim][PF6] | Cl | 24 | NRd |
4 | [bmim][BF4] | Cl | 3 | 28 |
5 | [bmim][SeO2(OCH3)] | Br | 3 | 57 |
6 | [bmim][SeO2(OCH3)] | 3 | 79 |
Entry | Indole 1a–c | 2a–c | Product 3a–i | Time (h) | Yield (%) b |
---|---|---|---|---|---|
1 | 3 | 78 (74)c | |||
2 | 2 | 73 | |||
3 | 3 | 55 | |||
4 | 3 | 68 | |||
5 | 2 | 65 | |||
6 | 3 | 53 | |||
7 | 3 | 74 | |||
8 | 2 | 65 | |||
9 | 3 | 62 |
Cycle | Time (h) | Yield of 3a (%) a |
---|---|---|
1 | 4 | 77 |
2 | 4 | 73 |
3 | 4 | 75 |
4 | 4 | 70 |
5 | 24 | 16 |
6 | 24 | trace |
3. Experimental
3.1. General
3.2. General Synthesis Procedure
4. Conclusions
Acknowledgments
References and Notes
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Zimmermann, E.G.; Thurow, S.; Freitas, C.S.; Mendes, S.R.; Perin, G.; Alves, D.; Jacob, R.G.; Lenardão, E.J. A Selenium-Based Ionic Liquid as a Recyclable Solvent for the Catalyst-Free Synthesis of 3-Selenylindoles. Molecules 2013, 18, 4081-4090. https://doi.org/10.3390/molecules18044081
Zimmermann EG, Thurow S, Freitas CS, Mendes SR, Perin G, Alves D, Jacob RG, Lenardão EJ. A Selenium-Based Ionic Liquid as a Recyclable Solvent for the Catalyst-Free Synthesis of 3-Selenylindoles. Molecules. 2013; 18(4):4081-4090. https://doi.org/10.3390/molecules18044081
Chicago/Turabian StyleZimmermann, Everton G., Samuel Thurow, Camilo S. Freitas, Samuel R. Mendes, Gelson Perin, Diego Alves, Raquel G. Jacob, and Eder J. Lenardão. 2013. "A Selenium-Based Ionic Liquid as a Recyclable Solvent for the Catalyst-Free Synthesis of 3-Selenylindoles" Molecules 18, no. 4: 4081-4090. https://doi.org/10.3390/molecules18044081