二氢苯并呋喃螺氧化吲哚的非对映选择性合成及其通过氧化吲哚核心的扩环转化为苯并呋喃喹啉酮。
Diastereoselective Synthesis of Dihydrobenzofuran Spirooxindoles and Their Transformation into Benzofuroquinolinones by Ring Expansion of Oxindole Core.
作者信息
Wang Feng, Pan Jia-Qi, Shi Ruo-Xian, Ning Rui, Wu Mingshu
机构信息
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China.
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China.
出版信息
J Org Chem. 2024 Apr 5;89(7):5142-5147. doi: 10.1021/acs.joc.3c02956. Epub 2024 Mar 28.
A mild and efficient approach for the diastereoselective synthesis of dihydrobenzofuran spirooxindoles using 3-chlorooxindoles and imines is presented. This process involves a formal [4 + 1] annulation, yielding the product with excellent diastereoselectivity. Furthermore, a novel method for constructing benzofuroquinolinone scaffolds through the ring expansion of oxindoles has been established. This method involves a lactam ring expansion to the quinolinone skeleton. Besides, a one-pot procedure for creating benzofuroquinolinone scaffolds from 3-chlorooxindoles and imines is also provided.
介绍了一种使用3-氯氧化吲哚和亚胺对二氢苯并呋喃螺氧化吲哚进行非对映选择性合成的温和有效方法。该过程涉及形式上的[4 + 1]环化反应，以优异的非对映选择性得到产物。此外，还建立了一种通过氧化吲哚扩环构建苯并呋喃喹啉酮骨架的新方法。该方法涉及内酰胺环向喹啉酮骨架的扩环。此外，还提供了一种由3-氯氧化吲哚和亚胺一锅法制备苯并呋喃喹啉酮骨架的方法。
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