Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions

Autor: Expédite Yen-Pon, Kendall N. Houk, Davide Audisio, Pier Alexandre Champagne, Frédéric Taran, Sandra Gabillet, Grégory Pieters, Gilles Muller, Lucie Plougastel, Mizuki Johnson, Pierre Thuéry

Publikováno v: Journal of the American Chemical Society, vol 141, iss 4

The first approach to pyrazole-containing helicenes via sydnone-aryne [3 + 2]-cycloaddition is described. An unprecedented regioselectivity in the cycloaddition step toward the more sterically constrained product was observed in the presence of exten

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4da66897b1334ac2c7ef7b421dbff82b
https://doi.org/10.1021/jacs.8b11465

Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes

Autor: Karine Porte, Margaux Riomet, Sabrina Bernard, Davide Audisio, Elodie Decuypere, Lucie Plougastel, Sergii Kolodych, Frédéric Taran

Publikováno v: Chemistry - A European Journal. 24:8535-8541

Emerging applications in the field of chemical biology are currently limited by the lack of bioorthogonal reactions allowing both removal and linkage of chemical entities on complex biomolecules. We recently discovered a novel reaction between iminos

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::72253078aa97a3f93ce6d117a0a91176
https://doi.org/10.1002/chem.201801163

Fluorogenic probes based on polycyclic sydnone scaffolds

Autor: Lucie Plougastel, Davide Audisio, Expédite Yen-Pon, Frédéric Taran, Diana Lamaa

Publikováno v: Tetrahedron
Tetrahedron, Elsevier, 2020, 76, pp.131250-. ⟨10.1016/j.tet.2020.131250⟩
Tetrahedron, 2020, 76, pp.131250-. ⟨10.1016/j.tet.2020.131250⟩

We report the synthesis, photophysical characterization and kinetics of a series of polycyclic sydnone derivatives as a potential new class of fluorogenic clickable reagents. After strain-promoted cycloaddition with cyclooctyne BCN, the fluorescence

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6ae6ea7eb45cc4d1702b41fc66dd4f36
https://doi.org/10.1016/j.tet.2020.131250

One-Pot Synthesis of 1,4-Disubstituted Pyrazoles from Arylglycines via Copper-Catalyzed Sydnone–Alkyne Cycloaddition Reaction

Autor: Simon Specklin, Elodie Decuypere, Soifia Aliani, Frédéric Taran, Lucie Plougastel

Publikováno v: The Journal of Organic Chemistry. 79:7772-7777

A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b3d36191cb1cea4709870c779451f5b0
https://doi.org/10.1021/jo501420r

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

Autor: Oleksandr Koniev, Lucie Plougastel, Christophe Créminon, Elodie Decuypere, Frédéric Taran, Alain Wagner, Sergii Kolodych, Simon Specklin, David-Alexandre Buisson

Publikováno v: Chem. Commun.. 50:9376-9378

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly s

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::693e8f0342b318cf5ca0fef0bb3462b9
https://doi.org/10.1039/c4cc03816a