Catalyst-Free Regio- and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco-friendly Solvent 2-Methyltetrahydrofuran

Gu, Xiaodong1; Du, Qingwei2; Song, Weijian2; Wang, Jun (Joelle)1

2022-12-01

10.1002/cjoc.202200550

CHINESE JOURNAL OF CHEMISTRY   影响因子和分区

1001-604X

1614-7065

An efficient and practical synthesis of heterocyclic nucleosides is developed by a catalyst-free highly regioselective and diastereoselective [3+2] annulation of alpha-purine-substituted acrylates with nitrones. The reaction operates with excellent functional group tolerance, very mild reaction conditions, and with the green, sustainable, and eco-friendly 2-methyltetrahydrofuran (2-MeTHF) as solvent. Compared with other reactions of electron-deficient olefin dipolarophiles with nitrones, different regioselective cycloaddition products were observed in this work. This 1,3-dipolar cycloaddition reaction gives a series of isoxazolidinyl nucleosides in good to excellent yields with promising applications in biochemistry and medicinal chemistry.

Heterocycle Nucleoside Catalyst-free Annulation Regioselectivity Synthetic methods Cycloaddition

SCI ; IC ; CCR

英语

其他

Chemistry

Chemistry, Multidisciplinary

WOS:000897579500001

WILEY-V C H VERLAG GMBH

CHEMISTRY

Web of Science

1.Hong Kong Baptist Univ, Dept Chem, Kowloon, Hong Kong, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

Gu, Xiaodong,Du, Qingwei,Song, Weijian,et al. Catalyst-Free Regio- and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco-friendly Solvent 2-Methyltetrahydrofuran[J]. CHINESE JOURNAL OF CHEMISTRY,2022,41(2).

Gu, Xiaodong,Du, Qingwei,Song, Weijian,&Wang, Jun .(2022).Catalyst-Free Regio- and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco-friendly Solvent 2-Methyltetrahydrofuran.CHINESE JOURNAL OF CHEMISTRY,41(2).

Gu, Xiaodong,et al."Catalyst-Free Regio- and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco-friendly Solvent 2-Methyltetrahydrofuran".CHINESE JOURNAL OF CHEMISTRY 41.2(2022).