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Convenient Synthesis of 671213-Tetrahydro-5H-Cyclohepta21-b:34-b’diindole Derivatives Mediated by Hypervalent Iodine (III) Reagent

机译:方便的合成由高价碘(III)试剂介导的671213-四氢-5H-环庚基21-b:34-b二吲哚衍生物

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摘要

Bisindolyl alkaloids represent a large family of natural and synthetic products that display various biological activities. Among the bisindole compounds, 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindoles have received little attention. Only two methods have been developed for the construction of the 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindole scaffold thus far, including the classical Fischer indole synthesis conducted by reacting indole-fused cycloheptanone and hydrazines, and the condensation reaction to build the seven-membered ring. Here, we report for the first time a new route to synthesize 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindoles through intramolecular oxidative coupling of 1,3-di(1H-indol-3-yl)propanes in the presence of PIFA, DDQ and TMSCl with moderate to excellent yields.
机译:Bisindolyl生物碱代表了一大类天然和合成产品,具有各种生物活性。在双吲哚化合物中,很少有人关注6,7,12,13-四氢-5H-环庚[2,1-b:3,4-b']二吲哚。迄今为止,仅开发了两种方法来构建6,7,12,13-四氢-5H-环庚[2,1-b:3,4-b']二吲哚支架,包括进行的经典Fischer吲哚合成通过与吲哚稠合的环庚酮和肼反应,再进行缩合反应,形成七元环。在这里,我们首次报告了通过1,3-分子内氧化偶联合成6,7,12,13-tetrahydro-5H-cyclohepta [2,1-b:3,4-b']二吲哚的新途径在PIFA,DDQ和TMSC1存在下的二(1H-吲哚-3-基)丙烷,产率中等至优异。

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