{"title":"Chemoselective synthesis of multisubstituted pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione through a cascade reaction","authors":"Abdolali Alizadeh, Reihaneh Moterassed","doi":"10.1007/s13738-024-03023-9","DOIUrl":null,"url":null,"abstract":"<div><p>A simple and efficient protocol for direct synthesis of multisubstituted 6-alkyl-4-chromenyl-1-aryl-3,4-dihydro-1<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridine-2,5,7(6<i>H</i>)-trione derivatives is presented by a cascade reaction of 3-formylchromones, Meldrum’s acid and <i>α</i>-aminomaleimides as readily accessible starting materials. In this chemoselective, metal catalyst-free approach Michael addition/intramolecular cyclization and elimination of acetone and carbon dioxide occur consecutively. The significant advantages of this strategy are creating a C–N and a C–C bond, short reaction times, excellent yields (68–80%), and a metal-free catalyst. </p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div><div><p>A simple and efficient protocol for direct synthesis of multisubstituted 6-alkyl-4-chromenyl-1-aryl-3,4-dihydro-1<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridine-2,5,7(6<i>H</i>)-trione derivatives is presented by a cascade reaction of 3-formylchromones, Meldrum’s acid and <i>α</i>-aminomaleimides as readily accessible starting materials.</p></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2024-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Iranian Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13738-024-03023-9","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
A simple and efficient protocol for direct synthesis of multisubstituted 6-alkyl-4-chromenyl-1-aryl-3,4-dihydro-1H-pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione derivatives is presented by a cascade reaction of 3-formylchromones, Meldrum’s acid and α-aminomaleimides as readily accessible starting materials. In this chemoselective, metal catalyst-free approach Michael addition/intramolecular cyclization and elimination of acetone and carbon dioxide occur consecutively. The significant advantages of this strategy are creating a C–N and a C–C bond, short reaction times, excellent yields (68–80%), and a metal-free catalyst.
Graphical Abstract
A simple and efficient protocol for direct synthesis of multisubstituted 6-alkyl-4-chromenyl-1-aryl-3,4-dihydro-1H-pyrrolo[3,4-b]pyridine-2,5,7(6H)-trione derivatives is presented by a cascade reaction of 3-formylchromones, Meldrum’s acid and α-aminomaleimides as readily accessible starting materials.
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JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.
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