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铁介导的由β-硝基苯乙烯一锅法合成3,5-二芳基吡啶

Iron-Mediated One-Pot Synthesis of 3,5-Diarylpyridines from β-Nitrostyrenes.

作者信息

Sathish Manda, Chetna Jadala, Hari Krishna Namballa, Shankaraiah Nagula, Alarifi Abdullah, Kamal Ahmed

机构信息

Medicinal Chemistry & Pharmacology, CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007, India.

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER) , Hyderabad 500 037, India.

出版信息

J Org Chem. 2016 Mar 4;81(5):2159-65. doi: 10.1021/acs.joc.5b02712. Epub 2016 Feb 12.

Abstract

An operationally simple and mild one-pot protocol for the synthesis of a variety of 3,5-diarylpyridines from β-nitrostyrenes was achieved by using elemental iron. This reaction proceeds via reduction of the nitro group, resulting in in situ imine formation followed by trimolecular condensation with concomitant debenzylative aromatization. By employing this method, a series of symmetrical and unsymmetrical 3,5-diarylpyridines were synthesized with good to excellent yields. In addition, this method was also utilized for the synthesis of Sch-21418, an anti-inflammatory agent on gram scale.

摘要

通过使用单质铁,实现了一种操作简单且温和的一锅法协议,用于从β-硝基苯乙烯合成多种3,5-二芳基吡啶。该反应通过硝基的还原进行,导致原位形成亚胺,随后进行三分子缩合并伴随脱苄基芳构化。通过采用这种方法,以良好至优异的产率合成了一系列对称和不对称的3,5-二芳基吡啶。此外,该方法还用于克级规模合成抗炎剂Sch-21418。

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