Synthesis of Cycloalkanoindoles by an Unusual DAST-Triggered Rearrangement Reaction
作者:Giuseppe Giannini、Mauro Marzi、Gian Piero Moretti、Sergio Penco、Maria Ornella Tinti、Silvia Pesci、Francesco Lazzaro、Francesco De Angelis
DOI:10.1002/ejoc.200300738
日期:2004.6
A series of 1,1-bis(indol-3-yl) and 1-(indol-2-yl)-1-(indol-3-yl)-ψ-hydroxyalkanes, prepared from the corresponding indole derivatives and suitable hydroxyaldehydes via routine coupling reactions, were treated with DAST (diethylaminosulfur trifluoride) under mild conditions, to generate a small library of cycloalkanoindoles. Irrespective of the substitution pattern, i.e. whether they are symmetrical
一系列 1,1-双(吲哚-3-基) 和 1-(吲哚-2-基)-1-(吲哚-3-基)-ψ-羟基烷烃,由相应的吲哚衍生物和合适的羟基醛通过以下方式制备常规偶联反应,在温和条件下用 DAST(二乙氨基三氟化硫)处理,以生成一个小的环烷烃吲哚库。无论取代模式如何,即它们是对称的还是不对称的衍生物,都会产生相同的产物混合物,其中四氢-1H-咔唑和六氢环庚[b]吲哚支架被一个吲哚-3-基核取代环烷烃部分的两个 α-碳原子。因此,提出了对共同反应中间体的预测的反应机理的推测。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)