Gupta Ekta, Nair Sindoori R, Kant Ruchir, Mohanan Kishor
Academy of Scientific and Innovative Research , New Delhi 110001 , India.
J Org Chem. 2018 Dec 7;83(23):14811-14819. doi: 10.1021/acs.joc.8b02504. Epub 2018 Nov 21.
An efficient three-component protocol for the synthesis of trifluoromethylated spiro-isoxazolidine-oxindoles has been developed. This approach employs the 1,3-dipolar cycloaddition of trifluoromethyl nitrone, generated in situ from trifluorodiazoethane and nitrosoarene, with phenacylideneoxindoles. A range of phenacyclideneoxindoles and nitrosoarenes can be subjected to this reaction to generate the spiro-isoxazolidine-oxindole derivatives. The reductive ring-opening reaction of isoxazolidines carried out to demonstrate the synthetic potential of our strategy resulted in an interesting rearrangement to yield pyrroloquinoline derivatives.
已开发出一种高效的三组分合成三氟甲基化螺异恶唑烷-氧化吲哚的方法。该方法采用由三氟重氮乙烷和亚硝基芳烃原位生成的三氟甲基硝酮与苯甲酰亚甲基氧化吲哚进行1,3-偶极环加成反应。一系列苯甲酰亚甲基氧化吲哚和亚硝基芳烃可进行此反应以生成螺异恶唑烷-氧化吲哚衍生物。进行异恶唑烷的还原开环反应以证明我们策略的合成潜力，结果产生了有趣的重排反应，生成吡咯并喹啉衍生物。
