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Organocatalytic aza-Michael Reaction to 3-Vinyl-1,2,4-triazines as a Valuable Bifunctional Platform

Abstract : An unprecedented catalytic aza-Michael addition to substituted 3-vinyl-1,2,4-triazines, as original bifunctional platforms for the domino conjugate addition inverse-electron-demand hetero-Diels–Alder/retro-Diels–Alder (ihDA/rDA) reaction, was achieved using the highly acidic triflimide as an organocatalyst. Based on the use of alkoxyamine nucleophiles, this sequence not only highlights a rare example of the catalytic aza-Michael reaction to alkenylazaarenes but also proves to be useful for the elaboration of an array of biorelevant tetrahydro-[1,6]-naphthyridines.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02197289
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, July 30, 2019 - 11:35:30 AM
Last modification on : Thursday, July 2, 2020 - 3:29:34 AM

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Floris Buttard, Clément Berthonneau, Marie-Aude Hiebel, Jean-François Brière, Franck Suzenet. Organocatalytic aza-Michael Reaction to 3-Vinyl-1,2,4-triazines as a Valuable Bifunctional Platform. Journal of Organic Chemistry, American Chemical Society, 2019, 84 (6), pp.3702-3714. ⟨10.1021/acs.joc.9b00141⟩. ⟨hal-02197289⟩

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