Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Artem N. Fakhrutdinov, Mikhail P. Egorov
{"title":"First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings","authors":"Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Artem N. Fakhrutdinov, Mikhail P. Egorov","doi":"10.1016/j.mencom.2024.10.030","DOIUrl":null,"url":null,"abstract":"<div><div>The new type of four-component tandem Knoevenagel–Michael reaction was found: isatins, barbituric acids, malononitrile and morpholine at ambient temperature and without catalysts selectively form new non-symmetrical ionic scaffold, namely, morpholin-4-ium 5-(3-dicyanomethyl-2-oxoindolin-3-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydropyrimidin-4-olate derivatives, in 80-98% yields. Their structure was confirmed using 2D NMR such as <sup>1</sup>H-<sup>1</sup>H COSY, <sup>1</sup>H-<sup>13</sup>C HSQC, and <sup>1</sup>H-<sup>13</sup>C HMBC correlation experiments. The products seem promising as they contain three different pharmacologically active heterocyclic rings.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 865-867"},"PeriodicalIF":1.8000,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Mendeleev Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0959943624003286","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
The new type of four-component tandem Knoevenagel–Michael reaction was found: isatins, barbituric acids, malononitrile and morpholine at ambient temperature and without catalysts selectively form new non-symmetrical ionic scaffold, namely, morpholin-4-ium 5-(3-dicyanomethyl-2-oxoindolin-3-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydropyrimidin-4-olate derivatives, in 80-98% yields. Their structure was confirmed using 2D NMR such as 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC correlation experiments. The products seem promising as they contain three different pharmacologically active heterocyclic rings.
期刊介绍:
Mendeleev Communications is the journal of the Russian Academy of Sciences, launched jointly by the Academy of Sciences of the USSR and the Royal Society of Chemistry (United Kingdom) in 1991. Starting from 1st January 2007, Elsevier is the new publishing partner of Mendeleev Communications.
Mendeleev Communications publishes short communications in chemistry. The journal primarily features papers from the Russian Federation and the other states of the former USSR. However, it also includes papers by authors from other parts of the world. Mendeleev Communications is not a translated journal, but instead is published directly in English. The International Editorial Board is composed of eminent scientists who provide advice on refereeing policy.