{"title":"Synthesis and structural features of new push-pull enamines, 5-aryl-3-[(dimethylamino)methylidene]furan-2(3H)-ones","authors":"A. S. Tikhomolova, A. Yu. Yegorova","doi":"10.1007/s11172-024-4351-2","DOIUrl":null,"url":null,"abstract":"<p>Conditions were optimized for the synthesis of dimethylaminomethylidene derivatives of furan-2(3<i>H</i>)-ones. This synthesis is based on the reaction of arylfuran-2(3<i>H</i>)-ones and dimethylformamide dimethyl acetal occurring at the methylene group of furanone ring. Effects of the solvent nature and the type of activation (heating at either atmospheric or elevated pressure in a sealed vessel) on the reaction rate and product yields were estimated. NOE NMR experiment allowed us to confirm the existence of 5-aryl-3-[(dimethylamino)methylidene]furan-2(3<i>H</i>)-ones in the form of <i>E</i>-isomers. The structure of one among the products was additionally confirmed using single crystal X-ray diffraction analysis.</p>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-09-19","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/s11172-024-4351-2","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Conditions were optimized for the synthesis of dimethylaminomethylidene derivatives of furan-2(3H)-ones. This synthesis is based on the reaction of arylfuran-2(3H)-ones and dimethylformamide dimethyl acetal occurring at the methylene group of furanone ring. Effects of the solvent nature and the type of activation (heating at either atmospheric or elevated pressure in a sealed vessel) on the reaction rate and product yields were estimated. NOE NMR experiment allowed us to confirm the existence of 5-aryl-3-[(dimethylamino)methylidene]furan-2(3H)-ones in the form of E-isomers. The structure of one among the products was additionally confirmed using single crystal X-ray diffraction analysis.
对合成呋喃-2(3H)-酮二甲胺亚甲基衍生物的条件进行了优化。该合成基于芳基呋喃-2(3H)-酮和二甲基甲酰胺二甲基缩醛在呋喃酮环的亚甲基上发生的反应。我们估算了溶剂性质和活化类型（在密封容器中常压或高压加热）对反应速率和产物产量的影响。NOE NMR 实验证实了 5-芳基-3-[(二甲基氨基)亚甲基]呋喃-2(3H)-酮以 E 异构体的形式存在。此外，我们还利用单晶 X 射线衍射分析证实了其中一种产品的结构。
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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