Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 36, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200843
Keywords
Cycloadditions; Deep Eutectic Solvents; Enolates; Green chemistry; Nitrogen heterocycles
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Funding
- University of Bari Aldo Moro [2017A5HXFC_002]
- Interuniversity Consortium C.I.N.M.P.I.S.
- Ministero dell'Universita e della Ricerca (MUR-PRIN)
- Universita degli Studi di Bari Aldo Moro within the CRUI-CARE Agreement
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A metal-free and environmentally friendly approach was developed for the synthesis of important 1,2,3-triazole compounds. This method not only allows for high-yield synthesis of target products at room temperature and under aerobic conditions, but also enables the synthesis of pharmaceutically relevant triazole derivatives through a one-pot process, simplifying the synthetic steps.
An eco-friendly metal-free protocol was developed for the regioselective synthesis of densely functionalized 1,2,3-triazoles through a 1,3-dipolar cycloaddition reaction of alkanone enolates with azides performed in the environmentally responsible choline chloride/urea or choline acetate/urea eutectic mixture. This approach displays a broad substrate scope, straightforwardly furnishing the desired triazoles (including the challenging phenolic derivatives) in yields of up to 98 %, while working at room temperature and under aerobic conditions. The practicability of the method is exemplified by the sustainable synthesis of some pharmaceutically relevant triazole derivatives carried out via telescoped, one-pot cycloaddition/reduction processes in the same eutectic mixture without any halfway isolation/purification step of intermediates.
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