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Metal-catalyzed dehydrogenative synthesis of pyrroles and indoles from alcohols

机译：金属催化醇催化脱氢合成吡咯和吲哚

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摘要

This review is focused on the synthesis of various classes of pyrroles and indoles from alcohols as substrates or intermediates. Metal-induced dehydrogenation converts primary or secondary alcohols into the related carbonyl compounds (aldehydes or ketones), which can undergo in situ inter- or intramolecular attack by a carbon or nitrogen nucleophile to afford a new C-C or C-N bond, respectively. The formation of these bonds is the key step in the construction of the pyrrole and indole framework. Thus, pyrroles are obtained in good yields by dehydrogenative cyclization of beta-hydroxyenamines, and dehydrogenative N-heterocyclization of amines with diols, High yields of pyrroles are also obtained by reacting 2 amino alcohols with alcohols or ketones. Relevant is also the synthesis of pyrroles by a three-component reaction. Indoles are formed in high yields by intramolecular cyclization of 2-amino- and 2-nitrophenylethyl alcohols, and 2-aminobenzyl alcohols. Moreover, indole derivatives are also conveniently obtained by reaction of glycols or alcohols with anilines or phenyl hydrazine, respectively. (C) 2016 Elsevier B.V. All rights reserved.
机译：这篇综述集中在以醇为底物或中间体合成各种类型的吡咯和吲哚。金属诱导的脱氢作用将伯醇或仲醇转化为相关的羰基化合物（醛或酮），这些羰基化合物可通过碳或氮亲核试剂进行原位分子间或分子内攻击，分别提供新的C-C或C-N键。这些键的形成是构建吡咯和吲哚骨架的关键步骤。因此，通过β-羟基胺的脱氢环化，以及胺与二醇的脱氢N-杂环，可以以高收率获得吡咯。通过使两种氨基醇与醇或酮反应，也可以获得高产率的吡咯。通过三组分反应合成吡咯也是相关的。通过2-氨基-和2-硝基苯基乙基醇和2-氨基苄基醇的分子内环化以高收率形成吲哚。而且，吲哚衍生物也可以方便地通过二醇或醇分别与苯胺或苯基肼反应而获得。 （C）2016 Elsevier B.V.保留所有权利。

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