Paraskevi-Kleio Anastasiou, Michael Fragkiadakis, Maria Thomaidi, Konstantinos G. Froudas, Constantinos G. Neochoritis
{"title":"Navigating Unexplored Territories of the Interrupted Ugi and Passerini Reactions toward Peptidomimetics","authors":"Paraskevi-Kleio Anastasiou, Michael Fragkiadakis, Maria Thomaidi, Konstantinos G. Froudas, Constantinos G. Neochoritis","doi":"10.1021/acs.orglett.4c04810","DOIUrl":null,"url":null,"abstract":"Interrupted reactions redirect established processes, often resulting in unexpected and novel outcomes. By employing a building block containing both acidic and oxo functionalities tethered to the same carbon, we uncovered interrupted variants of the Ugi and Passerini reactions. More than 20 derivatives with a peptide-like framework have been synthesized, demonstrating the broad scope and versatility of these reactions. Additional studies explored the use of various nucleophiles and postmodifications to expand even more the chemical diversity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"137 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04810","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
Interrupted reactions redirect established processes, often resulting in unexpected and novel outcomes. By employing a building block containing both acidic and oxo functionalities tethered to the same carbon, we uncovered interrupted variants of the Ugi and Passerini reactions. More than 20 derivatives with a peptide-like framework have been synthesized, demonstrating the broad scope and versatility of these reactions. Additional studies explored the use of various nucleophiles and postmodifications to expand even more the chemical diversity.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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