Buttard Floris, Berthonneau Clément, Hiebel Marie-Aude, Brière Jean-François, Suzenet Franck
Université d'Orléans, CNRS, ICOA, UMR 7311 , Orléans 45067 , France.
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA , Rouen 76000 , France.
J Org Chem. 2019 Mar 15;84(6):3702-3714. doi: 10.1021/acs.joc.9b00141. Epub 2019 Mar 1.
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.
使用高酸性三氟甲磺酰亚胺作为有机催化剂，实现了对取代的3-乙烯基-1,2,4-三嗪前所未有的催化氮杂-Michael加成反应，该反应作为多米诺共轭加成逆电子需求杂环Diels-Alder/逆Diels-Alder（ihDA/rDA）反应的原始双功能平台。基于烷氧基胺亲核试剂的使用，该反应序列不仅突出了对烯基氮杂芳烃进行催化氮杂-Michael反应的罕见实例，而且还证明可用于合成一系列与生物相关的四氢-[1,6]-萘啶。
