Harish Battu, Subbireddy Manyam, Obulesu Owk, Suresh Surisetti
Organic Synthesis and Process Chemistry , CSIR-Indian Institute of Chemical Technology (CSIR-IICT) , Hyderabad 500 007 , India.
Academy of Scientific and Innovative Research (AcSIR) , Ghaziabad 201002 , India.
Org Lett. 2019 Mar 15;21(6):1823-1827. doi: 10.1021/acs.orglett.9b00414. Epub 2019 Mar 5.
A unique intramolecular vinylogous Michael addition leading to the synthesis of heterocycles has been disclosed. Base-promoted one-pot sequential O-allylation of o-hydroxy-cinnamates or -cinnamonitrile or -chalcones with γ-bromocrotonates followed by an intramolecular conjugate addition of vinylogous Michael donors resulted in the formation of highly substituted benzofuran derivatives in good to excellent yields. The intramolecular event followed by two [1,3]-H shifts leading to aromatization appears to be the key to the success of this unprecedented transformation.
一种独特的分子内烯醇式迈克尔加成反应，可用于杂环化合物的合成，现已被公开。在碱促进下，邻羟基肉桂酸酯、肉桂腈或查耳酮与γ-溴巴豆酸酯进行一锅法顺序O-烯丙基化反应，随后分子内烯醇式迈克尔供体进行共轭加成反应，以良好至优异的产率生成了高度取代的苯并呋喃衍生物。分子内反应随后发生两次[1,3]-H迁移导致芳构化，这似乎是这一前所未有的转化成功的关键。
