{"title":"Construction of Benzoxazole and Isoquinoline Compounds via Base-Mediated Cyclization of Amino Acid Derivatives","authors":"Yilian Song, Zechao Liu, Chuangchuang Liu, Jingyu Zhang, Yingsheng Zhao","doi":"10.1021/acs.orglett.5c00736","DOIUrl":null,"url":null,"abstract":"Biological organisms contain bioactive macromolecules such as amino acids, which serve as basic materials for constructing cells and repairing tissues. Due to the unique properties of the fluorine atom, which can alter the structure of proteins and increase their lipophilicity, incorporating a fluorine atom into amino acids has become a research hotspot. In this study, ethyl 3-bromo-2-((diphenylmethylene)amino)-3,3-difluoropropanoate was synthesized from glycine derivatives. Under alkaline conditions, this compound reacted with 2-aminophenol to generate a benzoxazole-containing amino acid derivative. This method is simple to operate, without metal participation, and is performed under relatively eco-friendly reaction conditions, providing a novel approach for the synthesis of benzoxazole heterocycles.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-19","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.5c00736","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Biological organisms contain bioactive macromolecules such as amino acids, which serve as basic materials for constructing cells and repairing tissues. Due to the unique properties of the fluorine atom, which can alter the structure of proteins and increase their lipophilicity, incorporating a fluorine atom into amino acids has become a research hotspot. In this study, ethyl 3-bromo-2-((diphenylmethylene)amino)-3,3-difluoropropanoate was synthesized from glycine derivatives. Under alkaline conditions, this compound reacted with 2-aminophenol to generate a benzoxazole-containing amino acid derivative. This method is simple to operate, without metal participation, and is performed under relatively eco-friendly reaction conditions, providing a novel approach for the synthesis of benzoxazole heterocycles.
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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