Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors

• DOI: 10.1021/acs.joc.8b00872
• Publication Date: 2018-06-08T13:54:11Z
• Authors: Xi Feng; Xiaqiu Qiu; Huidan Huang; Jubo Wang; Xi Xu; Pengfei Xu; Ruijia Ge; Xiaojin Liu; Zhiyu Li; Jinlei Bian
• Keywords: Propargyl; Indoleamine 2,3-dioxygenase; Reaction conditions; Natural product

An efficient reaction utilizing propargyl carbonates through Claisen rearrangement to synthesize furanonaphthoquinones is described. The remarkable transformation exhibits excellent functional group tolerance, affording the target in moderate good yields (41–85%) under mild conditions. Scaled-up preparation of model product can make this a method choice for synthesis furanonaphthoquinone derivatives. resulting were evaluated as potential indoleamine 2,3-dioxygenase inhibitors vitro.