One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2024-06-21 DOI:10.1007/s11172-024-4242-6
A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. B. Valeev, A. N. Fakhrutdinov, M. N. Elinson, A. N. Vereshchagin
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Abstract

The present study describes a multicomponent synthesis of pyridinium derivatives of piperidin-2-ones from aromatic aldehydes, malononitriles, pyridines, haloacetates, and ammonium acetate. The synthesis occurs through the in situ formation of pyridinium ylide and involves the Knoevenagel—Michael—Mannich cyclization cascade. 1-[(3RS,4SR,6RS)-4,6-Diaryl-5,5-dicyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with three stereocenters and 1-[(3RS,4SR,5SR,6RS)-5-alkoxycarbonyl-4,6-diaryl-5-cyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with four stereocenters were synthesized.

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一锅形成六个键:含吡啶的哌啶-2-酮的伪六组份非对映选择性合成
本研究介绍了一种以芳香醛、丙二腈、吡啶、卤乙酸盐和乙酸铵为原料的哌啶-2-酮吡啶鎓衍生物的多组分合成方法。该合成是通过原位形成吡啶鎓酰化物,并涉及 Knoevenagel-Michael-Mannich 环化级联反应。合成了具有三个立体中心的 1-[(3RS,4SR,6RS)-4,6-二芳基-5,5-二氰基-2-氧代哌啶-3-基]吡啶-1-鎓卤化物和具有四个立体中心的 1-[(3RS,4SR,5SR,6RS)-5-烷氧基羰基-4,6-二芳基-5-氰基-2-氧代哌啶-3-基]吡啶-1-鎓卤化物。
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来源期刊
Russian Chemical Bulletin
Russian Chemical Bulletin 化学-化学综合
CiteScore
2.70
自引率
47.10%
发文量
257
审稿时长
3-8 weeks
期刊介绍: Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.
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