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首页> 外文期刊>Chemistry: A European journal >Direct Access to Fused Salicylaldehydes and Salicylketones from Tetraynes
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Direct Access to Fused Salicylaldehydes and Salicylketones from Tetraynes

机译：从Tetraynes直接进入融合的水杨醛和水杨酮

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摘要

A facile method for the synthesis of fused, multifunctionalized salicylaldehydes and salicylketones by a onepot, three-step cascade hexadehydro-Diels-Alder (HDDA) reaction of tetraynes followed by an intermolecular aldehyde/ ketone reaction and hydroxylation is reported. Target compounds were prepared by the condensation of malonates with 3-bromo-1-propyne, and the resulting 2,2-di(1-propyn- 3-yl)malonates underwent cross-coupling with phenylethynyl bromides to afford 2,2-di(5-phenyl-2,4-pentadiynyl)malonates, which underwent intramolecular cyclization to produce bicyclic salicylaldehydes. The overall transformation involves the formation of four new C-C bonds and one new C_(aryl)-O bond through both intramolecular and intermolecular reactions. The reaction is easy to perform, proceeds under mild conditions, and exhibits excellent regioselectivity. Water, a simple and readily available reagent, was employed as the OH source. A plausible reaction mechanism is proposed for this new annulation based on isotopic substitution experiments.
机译：据报道了一种通过单位合成融合，多官能化水杨醛和水杨酮，三步级联六十二二氧化物（HDDA）的四步级联羟基二氧化酯（HDDA）反应，然后进行分子分子醛/酮反应和羟基化。通过用3-溴-1-丙基缩合丙酸盐的缩合来制备靶化合物，并得到的2,2-DI（1-丙炔-3-基）丙二酸族与苯基乙炔基溴交联，以提供2,2-二（5-苯基-2,4-戊二炔基）丙二酸盐，其进行了分子内环化以产生双环水杨醛。整体转化涉及通过分子内和分子间反应形成四种新的C-C键和一个新的C_（芳基）-O键。反应易于进行，在温和条件下进行，并且表现出优异的区域选择性。水，简单且易于使用的试剂，用作OH源。基于同位素取代实验，提出了这种新的预报的合理反应机理。

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  • 来源
    《Chemistry: A European journal》 |2017年第17期|共8页
  • 作者

    Yimin Hu; Yadong Hu; Qiong Hu; Jie Ma; Shuang Lv; Baohua Liu; Shaowu Wang;

  • 作者单位

    Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 (P. R. Chin;

    Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 (P. R. Chin;

    Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 (P. R. Chin;

    Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 (P. R. Chin;

    Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 (P. R. Chin;

    Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 (P. R. Chin;

    Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 (P. R. Chin;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    condensed benzenoid compounds; crosscoupling; cyclization; hexadehydro-Diels-Alder reaction; salicylaldehyde derivatives;

    机译：浓缩的苯单形化合物;交叉耦合;环化;六十二醇二脉 - 桤木反应;水杨醛衍生物;

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