Suzuki Yamato, Ohta Yusuke, Oishi Shinya, Fujii Nobutaka, Ohno Hiroaki
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
J Org Chem. 2009 Jun 5;74(11):4246-51. doi: 10.1021/jo900681p.
Efficient methods for the synthesis of pyrrole-fused indole derivatives via domino copper-catalyzed multicomponent coupling and bis-cyclization have been developed. The mono- or bis-aminomethylated pyrroloindoles and dipyrrolopyridines were selectively obtained in moderate to excellent yields by a controlled Mannich-type reaction-cyclization of 4,6-diethynyl-1,3-phenylenediamine or its pyridine congener with paraformaldehyde and a secondary amine. The high-yielding bis-cyclization of terminal alkynes without using Mannich-type reactions is also presented.
已经开发出通过多米诺骨牌式铜催化多组分偶联和双环化反应合成吡咯并吲哚衍生物的有效方法。通过4,6-二乙炔基-1,3-苯二胺或其吡啶同系物与多聚甲醛和仲胺的可控曼尼希型反应环化，以中等至优异的产率选择性地获得了单氨基甲基化或双氨基甲基化的吡咯并吲哚和二吡咯并吡啶。还介绍了在不使用曼尼希型反应的情况下端炔的高产率双环化反应。
