{"title":"The Cascade Reaction Chemistry of Diazo Compounds with Intentionally Designed Alkene to Access Esterified Heterocycles","authors":"Shi-Cui Fang, Shao-Qun Cai, Pan-Pan Li, Zhi Yang, Jun-Fei Zhao, Hui-Xin Xiao, Yu-Tong Zhou, Xin-Ran Sun, Shi-Ya He, Fang Liu, Wu Liang, Bin Pan, Fei Du","doi":"10.1021/acs.orglett.4c03987","DOIUrl":null,"url":null,"abstract":"Exploration of the cascade reactivity of diazo compounds with alkenes is a challenging and largely unmet goal. Herein, we disclose a light-mediated de novo synthesis of esterified heterocycles under mild conditions. The reaction displays a broad functional group tolerance, including a wide variety of alkenes, diazo compounds, and some bioactive molecules. Importantly, the synthetic appeal was demonstrated for synthesizing indoleamine 2,3-dioxygenase inhibitor analogue, the deethylated derivative of natural product leucomidine C, and the anti-inflammatory agent AN669.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-01-02","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.4c03987","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
Exploration of the cascade reactivity of diazo compounds with alkenes is a challenging and largely unmet goal. Herein, we disclose a light-mediated de novo synthesis of esterified heterocycles under mild conditions. The reaction displays a broad functional group tolerance, including a wide variety of alkenes, diazo compounds, and some bioactive molecules. Importantly, the synthetic appeal was demonstrated for synthesizing indoleamine 2,3-dioxygenase inhibitor analogue, the deethylated derivative of natural product leucomidine C, and the anti-inflammatory agent AN669.
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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