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- Title
Catalyst‐Free Regio‐ and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco‐friendly Solvent 2‐Methyltetrahydrofuran<sup>†</sup>.
- Authors
Gu, Xiaodong; Du, Qingwei; Song, Weijian; Wang, Jun Joelle
- Abstract
Comprehensive Summary: An efficient and practical synthesis of heterocyclic nucleosides is developed by a catalyst‐free highly regioselective and diastereoselective [3+2] annulation of α‐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.
- Subjects
NUCLEOSIDE synthesis; PHARMACEUTICAL chemistry; ANNULATION; NITRONES; FUNCTIONAL groups; SOLVENTS; RING formation (Chemistry)
- Publication
Chinese Journal of Chemistry, 2023, Vol 41, Issue 2, p167
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202200550