Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters
Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters
复制标题
DOI：
10.1016/j.tetlet.2007.06.166
复制
发表时间：
2007-09-03
影响因子：
1.8
通讯作者：
Glennon, Richard A.
中科院分区：
文献类型：
--
作者：
De Oliveira, Eliseu O.;Brandt, Carlos A.;Glennon, Richard A.
本文首次用碘环化方法合成了新型的2-和n -取代的5-亚甲基-2-吡咯啉苯酰胺类化合物，以及2-、3-和n -取代的5-亚甲基-2-吡咯啉苯酰胺类化合物。该工艺的关键步骤是碘化亚甲基吡咯啉和碘化亚甲基吡咯啉中间体的合成。这些碘化物的官能团相互转化为它们的氨基类似物，然后通过EDC偶联到苯甲酸，得到上述吡咯烷/2-吡咯烷取代的苯酰胺，产率约为75%。(C) 2007 Elsevier Ltd.版权所有。
Novel 2-, and N-substituted 5-methylene-pyrrolidine benzamides and 2-, 3-, and N-substituted 5-methylene-2-pyrroline benzamides were synthesized for the first time in a straightforward manner and in good yields via iodocyclization of gamma- and alpha-alkenyl-beta-enaminoesters, respectively. The key step in the process is the synthesis of the methylene-pyrrolidine iodide and methylene-2-pyrroline iodide intermediates. Functional group inter-conversion of these iodides to their amino analogs, and their subsequent coupling to benzoic acids via EDC, afforded the above pyrrolidine/2-pyrroline-substituted benzamides in yields of around 75%. (C) 2007 Elsevier Ltd. All rights reserved.