Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones

Yulin Sun; Zhuoyuan Liu; Donghan Liu; Mingshuai Zhang; Longkun Chen; Zhangmengjie Chai; Xue-Bing Chen; Fuchao Yu

doi:10.1021/acs.joc.3c00925

Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones

J Org Chem. 2023 Aug 18;88(16):11627-11636. doi: 10.1021/acs.joc.3c00925. Epub 2023 Aug 9.

Authors

Yulin Sun¹, Zhuoyuan Liu¹, Donghan Liu¹, Mingshuai Zhang¹, Longkun Chen¹, Zhangmengjie Chai¹, Xue-Bing Chen^{1

2}, Fuchao Yu¹

Affiliations

¹ Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. China.
² College of Science, Honghe University, Mengzi 661199 Yunnan, P. R. China.

PMID: 37556793
DOI: 10.1021/acs.joc.3c00925

Abstract

Syntheses of highly functionalized 4-alkylated 1,4-dihydropyridines (1,4-DHPs) from cyclic ethers and enaminones via iron(II)-mediated oxidative free radical cascade C(sp³)-H bond functionalization/C(sp³)-O bond cleavage/cyclization reaction have been first developed. This novel synthetic strategy offers an alternative method for the construction of 1,4-DHPs by using esters as the C4 sources, as well as expands the application of ethers in heterocycle synthesis.