{"title":"Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles via annulation involving isatylidene malononitriles and benzylamines†","authors":"Issa Yavari , Mahmoud Ahmadi , Parisa Ravaghi , Ramin Mohsenzadeh","doi":"10.1039/d4ob01811g","DOIUrl":null,"url":null,"abstract":"<div><div>A cascade reaction utilizing benzylamines and two equivalents of isatylidene malononitriles in alcohols effectively produces dispiro[indoline-cyclopentapyrimidine-indoline] structures with high chemical yields, reaching up to 93%, and remarkable diastereoselectivity (dr ≥ 19 : 1). This one-pot synthesis, facilitated by nucleophilic solvent participation, provides a practical method for obtaining multicyclic dispiro-cyclopentene-linked bisoxindoles, generating four chiral centers in a diastereoselective fashion. The practical applicability of this approach was further illustrated through a gram-scale experiment, and the final product's structure was confirmed <em>via</em> single-crystal X-ray analysis, affirming the successful synthesis of the target compounds.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 11","pages":"Pages 2712-2720"},"PeriodicalIF":2.7000,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025000941","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/11 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A cascade reaction utilizing benzylamines and two equivalents of isatylidene malononitriles in alcohols effectively produces dispiro[indoline-cyclopentapyrimidine-indoline] structures with high chemical yields, reaching up to 93%, and remarkable diastereoselectivity (dr ≥ 19 : 1). This one-pot synthesis, facilitated by nucleophilic solvent participation, provides a practical method for obtaining multicyclic dispiro-cyclopentene-linked bisoxindoles, generating four chiral centers in a diastereoselective fashion. The practical applicability of this approach was further illustrated through a gram-scale experiment, and the final product's structure was confirmed via single-crystal X-ray analysis, affirming the successful synthesis of the target compounds.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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