受阿马酮生物合成启发的重氮霍克反应。
A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone.
机构信息
Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia.
College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
出版信息
Org Lett. 2022 Jan 21;24(2):490-495. doi: 10.1021/acs.orglett.1c03810. Epub 2022 Jan 7.
Abstract
Motivated by the biosynthesis of azamerone, we report the first example of a diazo-Hooker reaction, which involves the formation of a phthalazine ring system by the oxidative rearrangement of a diazoketone. Computational studies indicate that the diazo-Hooker reaction proceeds via an 8π-electrocyclization followed by ring contraction and aromatization. The biosynthetic origin of the diazoketone functional group was also chemically mimicked using a related natural product, naphterpin, as a model system.
摘要
受 azamerone 生物合成的启发，我们报告了首例重氮-Hooker 反应的实例，该反应通过氧化重氮酮的重排形成了邻苯二甲嗪环系统。计算研究表明，重氮-Hooker 反应通过 8π-电环化反应进行，随后进行环收缩和芳构化。还使用相关天然产物萘啶酮作为模型系统，通过化学模拟模拟了 diazoketone 官能团的生物合成起源。
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