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

Floris Buttard | Zendy; Clément Berthonneau | Zendy; MarieAude Hiebel | Zendy; JeanFrançois Brière | Zendy; Franck Suzenet | Zendy

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

Author(s) -

Floris Buttard,

Clément Berthonneau,

MarieAude Hiebel,

JeanFrançois Brière,

Franck Suzenet

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b00141

Subject(s) - bifunctional , chemistry , domino , conjugate , michael reaction , nucleophile , catalysis , combinatorial chemistry , organic chemistry , organocatalysis , enantioselective synthesis , mathematical analysis , mathematics

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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