通过酰胺斯迈尔斯重排反应由7-羟基香豆素合成7-氨基香豆素
Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement.
作者信息
Lippe Daniel S, Elghawy Omar, Zucker Adam M, Yanagawa Evan S K, Mathews Erin, Ahmed Yusef G, D'Elia Paige N, Bimson Sabrina, Walvoord Ryan R
机构信息
Department of Chemistry, Ursinus College, Collegeville, Pennsylvania 19426, United States.
出版信息
ACS Omega. 2022 Sep 21;7(39):35269-35279. doi: 10.1021/acsomega.2c04653. eCollection 2022 Oct 4.
N-Substituted 7-aminocoumarins can be synthesized from readily available 7-hydroxycoumarins via alkylation with α-bromoacetamides and subsequent tandem O → N Smiles rearrangement-amide hydrolysis. The key rearrangement sequence proceeds under mild conditions to provide convenient access to various -alkyl and -aryl products in moderate to high yields. The process is operationally simple, inexpensive, transition-metal-free, and can be telescoped into a one-pot process.
N-取代的7-氨基香豆素可以由容易获得的7-羟基香豆素通过与α-溴代乙酰胺烷基化，随后进行串联的O→N斯迈尔斯重排-酰胺水解反应来合成。关键的重排步骤在温和条件下进行，能以中等到高的产率方便地获得各种N-烷基和N-芳基产物。该过程操作简单、成本低廉、无需过渡金属，并且可以缩合为一锅法工艺。
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