{"title":"Five-Component [2 + 2 + 1 + 1] Tandem Benzannulation Leading to Multifunctionalized Aromatic Amines","authors":"Hexiang Wang, Shuting Li, Xiaoying Wu, Tiantian Chen, Wenjie Liu, Xiang Liu, Hua Cao","doi":"10.1021/acs.orglett.4c03299","DOIUrl":null,"url":null,"abstract":"An unprecedented five-component [2 + 2 + 1 + 1] benzannulation strategy for regioselective assembly of densely functionalized aromatic amines from two ynals, two malononitriles, and sodium sulfinates is established. The benzannulation protocol enables the efficient installation of five substituents on a benzene ring via the formation of multiple chemical bonds in a single operation, providing various multifunctionalized aromatic primary amines in moderate to good yields. Additionally, three-component [3 + 2 + 1] cycloaddition of malononitriles, ynals, and NH<sub>4</sub>SCN was also achieved to produce 2-amnopyridine derivatives with NH<sub>4</sub>SCN serving as an ammonia surrogate.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-11-01","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.4c03299","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
An unprecedented five-component [2 + 2 + 1 + 1] benzannulation strategy for regioselective assembly of densely functionalized aromatic amines from two ynals, two malononitriles, and sodium sulfinates is established. The benzannulation protocol enables the efficient installation of five substituents on a benzene ring via the formation of multiple chemical bonds in a single operation, providing various multifunctionalized aromatic primary amines in moderate to good yields. Additionally, three-component [3 + 2 + 1] cycloaddition of malononitriles, ynals, and NH4SCN was also achieved to produce 2-amnopyridine derivatives with NH4SCN serving as an ammonia surrogate.
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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