Synthesis of het(aryl) imidazole C-nucleoside analogues by CoFe2O4 NPs catalyzed muti-component coupling reaction

Fuyi Zhang; Yang Li; Fei Gao; Hong Liu; Yufen Zhao

doi:10.1016/j.carres.2019.03.013

Synthesis of het(aryl) imidazole C-nucleoside analogues by CoFe₂O₄ NPs catalyzed muti-component coupling reaction

Carbohydr Res. 2019 May 15:477:39-50. doi: 10.1016/j.carres.2019.03.013. Epub 2019 Apr 3.

Authors

Fuyi Zhang¹, Yang Li², Fei Gao², Hong Liu², Yufen Zhao³

Affiliations

¹ The College of Chemistry and Molecular Engineering, The Key Lab of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou, China. Electronic address: zhangfy@zzu.edu.cn.
² The College of Chemistry and Molecular Engineering, The Key Lab of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou, China.
³ The College of Chemistry and Molecular Engineering, The Key Lab of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou, China; Institute of Drug Discovery Technology, Ningbo University, Ningbo, China.

PMID: 30959446
DOI: 10.1016/j.carres.2019.03.013

Abstract

A general synthesis of hetaryl and aryl C-4(5) linked imidazole C-nucleoside analogues has been developed by the reaction of sugar alkynes with het(aryl) iodides, KMnO₄/TBAB oxidation and CoFe₂O₄ NPs catalyzed muti-component coupling of the corresponding diketones, NH₄OAc and aromatic aldehydes in one-pot. The sugar alkynes include pyranosides and furanosides with acid sensitive protecting groups. The het(aryl) iodides comprise iodoaromatics, iodoheterocycles, and sterically hindered iodoheteroaromatics.

Keywords: Muti-component coupling reaction; Sugar alkyne; het(aryl) imidazole C-nucleoside analogue.

MeSH terms

Catalysis
Cobalt / chemistry*
Ferric Compounds / chemistry*
Imidazoles / chemical synthesis*
Imidazoles / chemistry
Molecular Structure
Nanoparticles / chemistry*
Nucleosides / chemical synthesis*
Nucleosides / chemistry

Substances

Ferric Compounds
Imidazoles
Nucleosides
cobalt ferrite
Cobalt
imidazole