Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.
Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.
复制标题
DOI：
10.1021/co300003c
复制
发表时间：
2012-04-09
影响因子：
--
通讯作者：
Franz AK
中科院分区：
文献类型：
--
作者：
MacDonald JP;Badillo JJ;Arevalo GE;Silva-García A;Franz AK
提出了一种两步合成羟吲哚和螺羟吲哚的三唑衍生物的方法。使用一组常见的N-炔丙基化靛红，与亲核试剂和催化剂的不同组合的一系列机械上不同的立体选择性反应提供了获得不同的羟基-羟吲哚，螺吲哚酮和螺环恶唑啉结构的途径。然后使用铜催化的叠氮化物-炔环加成（CuAAC）反应将所得的N-炔丙基化羟吲哚转化为三唑。总的来说，这种策略提供了一个64个成员的中试规模的图书馆不同羟吲哚和螺羟吲哚。
A strategy for the efficient two-step synthesis of triazole derivatives of oxindoles and spirooxindoles is presented. Using a common set of N-propargylated isatins, a series of mechanistically-distinct stereoselective reactions with different combinations of nucleophiles and catalysts provide access to diverse hydroxy-oxindoles, spiroindolones, and spirocyclic oxazoline structures. The resulting N-propargylated oxindoles are then converted to triazoles using copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. Overall, this strategy affords a 64-member pilot-scale library of diverse oxindoles and spirooxindoles.