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. 2021 Feb 18;26(4):1074.
doi: 10.3390/molecules26041074.

Demonstration of Green Solvent Performance on O,S,N-Heterocycles Synthesis: Metal-Free Click Chemistry and Buchwald-Hartwig Coupling

Joana F Campos  1 , Manon Cailler  1 , Remi Claudel  1 , Benjamin Prot  1 , Thierry Besson  2 , Sabine Berteina-Raboin  1
Affiliations

Demonstration of Green Solvent Performance on O,S,N-Heterocycles Synthesis: Metal-Free Click Chemistry and Buchwald-Hartwig Coupling

Joana F Campos et al. Molecules. .

Abstract

The development of new and greener approaches to organic synthesis has been a trend in recent years. Continuing the latest publications of our team, in this work, we demonstrate the efficiency of three solvents: eucalyptol (1,8-cineole), cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF) for the synthesis of O,S,N-heterocyclic compounds.

Keywords: 2-methyltetrahydrofuran; O,S,N-heterocycles; cyclopentyl methyl ether; eucalyptol; green solvent; greener methodology.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Green solvents used in this work.
Figure 2
Figure 2
Structures of some Food and Drug Administration (FDA) approved drugs with heterocyclic scaffolds reported in this study.
Figure 3
Figure 3
Study of scope and limitations of Buchwald–Hartwig Coupling/Pyridine Dearomatization Sequence from methyl 3-aminothiophene-2-carboxylate. (a) methodology developped by Y.Monguchi et al. (2008) (b) work reported by our team in 2020.
Figure 4
Figure 4
Study of scope and limitations of Metal-free Click Chemistry from 7-amino-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester.
Figure 5
Figure 5
Study of scope and limitations of Metal-free Click Chemistry from methyl 6-amino-1H-indazole-7-carboxylate.
Figure 6
Figure 6
Study of scope and limitations of Metal-free Click Chemistry from methyl 3-amino-5-phenylthiophene-2-carboxylate.
Figure 7
Figure 7
Study of scope and limitations of Metal-free Click Chemistry from methyl 3-aminothiophene-2-carboxylate.
Figure 8
Figure 8
Study of scope and limitations of Metal-free Click Chemistry from methyl 4-amino-5-thiazolecarboxylate.
Figure 9
Figure 9
Study of scope and limitations of Buchwald–Hartwig Coupling/Pyridine Dearomatization Sequence from methyl 3-aminothiophene-2-carboxylate 1d.
Figure 10
Figure 10
Study of scope and limitations of Buchwald–Hartwig Coupling/Pyridine Dearomatization Sequence from methyl 3-amino-5-phenylthiophene-2-carboxylate.
Figure 11
Figure 11
Study of scope and limitations of Buchwald–Hartwig Coupling.
See this image and copyright information in PMC

References

    1. Clarke C.J., Tu W.-C., Levers O., Bröhl A., Hallett J.P. Green and Sustainable Solvents in Chemical Processes. Chem. Rev. 2018;118:747–800. doi: 10.1021/acs.chemrev.7b00571. - DOI - PubMed
    1. Laird T. Green Chemistry is Good Process Chemistry. Org. Process Res. Dev. 2012;16:1–2. doi: 10.1021/op200366y. - DOI
    1. Henderson R.K., Jiménez-González C., Constable D.J.C., Alston S.R., Inglis G.G.A., Fisher G., Sherwood J., Binks S.P., Curzons A.D. Expanding GSK’s solvent selection guide—embedding sustainability into solvent selection starting at medicinal chemistry. Green Chem. 2011;13:854–862. doi: 10.1039/c0gc00918k. - DOI
    1. Capello C., Fischer U., Hungerbühler K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007;9:927–934. doi: 10.1039/b617536h. - DOI
    1. Alfonsi K., Colberg J., Dunn P.J., Fevig T., Jennings S., Johnson T.A., Kleine H.P., Knight C., Nagy M.A., Perry D.A., et al. Green chemistry tools to influence a medicinal chemistry and research chemistry based organization. Green Chem. 2008;10:31–36. doi: 10.1039/B711717E. - DOI

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