Natalia N. Gibadullina , Aigul R. Mukhamedyarova , Aleksandr N. Lobov , Yuri S. Zimin , Vladimir A. Dokichev
{"title":"一种在钾、钠和铵氯化物促进下在水中合成 1,2,3,4-四氢吡啶和六氢咪唑并[1,2-a]吡啶的环保型方法","authors":"Natalia N. Gibadullina , Aigul R. Mukhamedyarova , Aleksandr N. Lobov , Yuri S. Zimin , Vladimir A. Dokichev","doi":"10.1016/j.tetlet.2024.155348","DOIUrl":null,"url":null,"abstract":"<div><div>A new one-pot method was developed for the synthesis of polyfunctional 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines by three-component reaction of ethyl 3-oxobutanoate with formaldehyde and primary amines occurring in water in the presence of electrolytes (NaCl, KCl, NH<sub>4</sub>Cl) at room temperature. This environmentally friendly method is highly atom economic, because the only by-products it gives are three water molecules. The effect of the structure of primary amines and reaction conditions on the degree of formation of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines was investigated.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155348"},"PeriodicalIF":1.5000,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An environmentally friendly method for the synthesis of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines in water promoted by potassium, sodium and ammonium chlorides\",\"authors\":\"Natalia N. Gibadullina , Aigul R. Mukhamedyarova , Aleksandr N. Lobov , Yuri S. Zimin , Vladimir A. Dokichev\",\"doi\":\"10.1016/j.tetlet.2024.155348\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A new one-pot method was developed for the synthesis of polyfunctional 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines by three-component reaction of ethyl 3-oxobutanoate with formaldehyde and primary amines occurring in water in the presence of electrolytes (NaCl, KCl, NH<sub>4</sub>Cl) at room temperature. This environmentally friendly method is highly atom economic, because the only by-products it gives are three water molecules. The effect of the structure of primary amines and reaction conditions on the degree of formation of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines was investigated.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"152 \",\"pages\":\"Article 155348\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-10-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S004040392400443X\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040392400443X","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
An environmentally friendly method for the synthesis of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines in water promoted by potassium, sodium and ammonium chlorides
A new one-pot method was developed for the synthesis of polyfunctional 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines by three-component reaction of ethyl 3-oxobutanoate with formaldehyde and primary amines occurring in water in the presence of electrolytes (NaCl, KCl, NH4Cl) at room temperature. This environmentally friendly method is highly atom economic, because the only by-products it gives are three water molecules. The effect of the structure of primary amines and reaction conditions on the degree of formation of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines was investigated.
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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