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Synthesis 2022; 54(09): 2298-2308
DOI: 10.1055/a-1730-7983
DOI: 10.1055/a-1730-7983
paper
Convenient and General Synthesis of C-3-Substituted Het(aryl)indole C-Nucleoside Analogues from Sugar Alkynes
We gratefully acknowledge the National Natural Science Foundation of China (No. 21772180, 21272219) for financial support.
Abstract
The synthesis of C-3-substituted het(aryl)indole C-nucleoside analogues bearing structurally diverse sugar moieties has been achieved by Sonogashira coupling of terminal sugar alkynes with het(aryl) iodides followed by heteroannulation of the corresponding sugar/het(aryl) alkynes with substituted 2-iodoanilines. This method is simple and general and is suitable for structurally diverse sugars and various het(aryl) iodides. The terminal sugar alkynes include furanosides, pyranosides, and acyclic sugars with sensitive groups and bulky substituents. The het(aryl) iodides involve iodobenzene, iodothiophene, iodobenzothiophene, and iodobenzofuran. Thirty-one examples are presented and the corresponding 2-het(aryl)indole C-nucleoside analogues are obtained in moderate to excellent yields.
Key words
C-3 substituted het(aryl)indole - C-nucleoside - analogue - sugar alkyne - heteroannulationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1730-7983.
- Supporting Information
Publication History
Received: 30 November 2021
Accepted after revision: 04 January 2022
Accepted Manuscript online:
04 January 2022
Article published online:
21 February 2022
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