A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. B. Valeev, A. N. Fakhrutdinov, M. N. Elinson, A. N. Vereshchagin
{"title":"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","authors":"A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. B. Valeev, A. N. Fakhrutdinov, M. N. Elinson, A. N. Vereshchagin","doi":"10.1007/s11172-024-4242-6","DOIUrl":null,"url":null,"abstract":"<p>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 <i>in situ</i> formation of pyridinium ylide and involves the Knoevenagel—Michael—Mannich cyclization cascade. 1-[(3<i>RS</i>,4<i>SR</i>,6<i>RS</i>)-4,6-Diaryl-5,5-dicyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with three stereocenters and 1-[(3<i>RS</i>,4<i>SR</i>,5<i>SR</i>,6<i>RS</i>)-5-alkoxycarbonyl-4,6-diaryl-5-cyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with four stereocenters were synthesized.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones\",\"authors\":\"A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. B. Valeev, A. N. Fakhrutdinov, M. N. Elinson, A. N. Vereshchagin\",\"doi\":\"10.1007/s11172-024-4242-6\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>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 <i>in situ</i> formation of pyridinium ylide and involves the Knoevenagel—Michael—Mannich cyclization cascade. 1-[(3<i>RS</i>,4<i>SR</i>,6<i>RS</i>)-4,6-Diaryl-5,5-dicyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with three stereocenters and 1-[(3<i>RS</i>,4<i>SR</i>,5<i>SR</i>,6<i>RS</i>)-5-alkoxycarbonyl-4,6-diaryl-5-cyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with four stereocenters were synthesized.</p>\",\"PeriodicalId\":756,\"journal\":{\"name\":\"Russian Chemical Bulletin\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-06-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Chemical Bulletin\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1007/s11172-024-4242-6\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s11172-024-4242-6","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones
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.
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.