LAQV@REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa , Campus de Caparica, 2829-516 Caparica, Portugal.
Org Lett. 2017 Oct 6;19(19):5118-5121. doi: 10.1021/acs.orglett.7b02403. Epub 2017 Sep 15.
A direct synthesis of several 1,2-disubstituted 4-, 5-, 6-, and 7-azaindoles from available amino-o-halopyridines is described. This procedure involves a palladium-catalyzed N-arylation followed by a Sonogashira reaction and subsequent cyclization in a one-pot manner, exhibiting a wide scope and compatibility with electron-withdrawing and electron-donating groups. The strategy represents an advancement in azaindole chemistry with a straightforward approach toward 1,2-disubstituted azaindoles, while avoiding complex N-arylations of hindered 2-substituted azaindoles and difficult purification steps of intermediates.
本文描述了一种从易得的氨基-o-卤代吡啶出发直接合成几种 1,2-二取代的 4-, 5-, 6-, 和 7-氮杂吲哚的方法。该方法涉及钯催化的 N-芳基化反应，随后进行 Sonogashira 反应和在一锅法中的后续环化反应，具有广泛的适用性和对吸电子和给电子基团的兼容性。该策略代表了氮杂吲哚化学的一项进展，提供了一种直接合成 1,2-二取代氮杂吲哚的方法，同时避免了位阻较大的 2-取代氮杂吲哚的复杂 N-芳基化反应和中间体的困难纯化步骤。
