Synthesis of C-ring hydrogenated sinomenine cinnamate derivatives via Heck reactions. Issue 11 (November 2019)

• Record Type: Journal Article
• Authors: Pan, Hongmei; Lu, Tong; Wu, Xuedan; Jiang, Chuan; Gu, Chengwen; Zhang, Kehua; Jin, Jie
• Is Part Of: Journal of chemical research. Volume 43:Issue 11/12(2019)
• Page Start: 469
• Page End: 473
• Publication Date: 2019-11
• Subjects: cinnamate -- halogenation -- Heck reaction -- sinomenine -- synthesis; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.1177/1747519819868201
• Languages: English
• ISSNs: 1747-5198

Abstract

The synthesis of C-ring hydrogenated sinomenine derivatives is accomplished from sinomenine by treatment with Zn-Hg/HCl, halogenation with NIS, and Heck reactions with various acrylates. A total of nine novel sinomenine cinnamate derivatives are obtained in 84%–93% yields. The structures of all the derivatives are characterized by 1 H NMR, 13 C NMR, and MS spectroscopy.