{"title":"含金刚烷基的汉茨多取代吡啶的合成","authors":"Mina Abkar Aras, Adeleh Moshtaghi Zonouz","doi":"10.1007/s00706-023-03164-2","DOIUrl":null,"url":null,"abstract":"<p>A one-step procedure has been developed for the synthesis of new Hantzsch poly-substituted pyridines from a three-component reaction of <i>N</i>-(adamantan-1-yl)acetoacetamide, aldehyde derivatives, ammonium acetate in ethanol in the presence of montmorillonite K10 catalyst under reflux conditions. The presence of adamantyl moiety in adamantyl acetoacetamide as an active methylene component leads to a strong steric hindrance and accelerates the oxidation of 1,4-dihydropyridines to the pyridine derivatives. The use of montmorillonite catalyst leads to a simple procedure of synthesis and short reaction times. As a result, facile workup, simple reaction procedure, good yields, and economical process are advantages of this one-pot multicomponent reaction.</p><h3 data-test=\"abstract-sub-heading\">Graphical abstract</h3>\n","PeriodicalId":19011,"journal":{"name":"Monatshefte für Chemie / Chemical Monthly","volume":"14 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of Hantzsch poly-substituted pyridines containing adamantyl moiety\",\"authors\":\"Mina Abkar Aras, Adeleh Moshtaghi Zonouz\",\"doi\":\"10.1007/s00706-023-03164-2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>A one-step procedure has been developed for the synthesis of new Hantzsch poly-substituted pyridines from a three-component reaction of <i>N</i>-(adamantan-1-yl)acetoacetamide, aldehyde derivatives, ammonium acetate in ethanol in the presence of montmorillonite K10 catalyst under reflux conditions. The presence of adamantyl moiety in adamantyl acetoacetamide as an active methylene component leads to a strong steric hindrance and accelerates the oxidation of 1,4-dihydropyridines to the pyridine derivatives. The use of montmorillonite catalyst leads to a simple procedure of synthesis and short reaction times. As a result, facile workup, simple reaction procedure, good yields, and economical process are advantages of this one-pot multicomponent reaction.</p><h3 data-test=\\\"abstract-sub-heading\\\">Graphical abstract</h3>\\n\",\"PeriodicalId\":19011,\"journal\":{\"name\":\"Monatshefte für Chemie / Chemical Monthly\",\"volume\":\"14 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-02-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Monatshefte für Chemie / Chemical Monthly\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1007/s00706-023-03164-2\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte für Chemie / Chemical Monthly","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1007/s00706-023-03164-2","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Synthesis of Hantzsch poly-substituted pyridines containing adamantyl moiety
A one-step procedure has been developed for the synthesis of new Hantzsch poly-substituted pyridines from a three-component reaction of N-(adamantan-1-yl)acetoacetamide, aldehyde derivatives, ammonium acetate in ethanol in the presence of montmorillonite K10 catalyst under reflux conditions. The presence of adamantyl moiety in adamantyl acetoacetamide as an active methylene component leads to a strong steric hindrance and accelerates the oxidation of 1,4-dihydropyridines to the pyridine derivatives. The use of montmorillonite catalyst leads to a simple procedure of synthesis and short reaction times. As a result, facile workup, simple reaction procedure, good yields, and economical process are advantages of this one-pot multicomponent reaction.
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