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Organocatalyzed Thia-Michael Addition and Sequential Inverse Electron Demanding Diels-Alder Reaction to 3-Vinyl-1,2,4- triazine Platforms

Abstract : This work highlights the use of 3‐vinyl‐1,2,4‐triazines as original thia‐Michael acceptors and inverse electron demanding Diels‐Alder platforms en route to new 7,8‐dihydro‐5H‐thiopyrano[4,3‐b ]pyridines. The required but rather unstable propargylthiol nucleophiles were successfully generated in‐situ upon an innovative DBU‐catalyzed methanolysis event of the corresponding propargyl thioacetate derivatives.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046260
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:39:29 PM
Last modification on : Monday, July 27, 2020 - 3:15:05 PM

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Clément Berthonneau, F. Buttard, M.-A. Hiebel, F. Suzenet, Jean-François Brière. Organocatalyzed Thia-Michael Addition and Sequential Inverse Electron Demanding Diels-Alder Reaction to 3-Vinyl-1,2,4- triazine Platforms. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2017, 359 (23), pp.4106-4110. ⟨10.1002/adsc.201700831⟩. ⟨hal-02046260⟩

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