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一锅法通过糖炔、吡啶和α-溴代羰基化合物的偶联高效合成新型吲哚嗪 C-核苷类似物。

Efficient synthesis of novel indolizine C-nucleoside analogues via coupling of sugar alkynes, pyridines and α-bromo carbonyl compounds in one pot.

机构信息

Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001, China.

Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001, China.

出版信息

Carbohydr Res. 2021 Jul;505:108337. doi: 10.1016/j.carres.2021.108337. Epub 2021 May 24.

DOI:10.1016/j.carres.2021.108337
PMID:34058545
Abstract

The synthesis of novel indolizine C-nucleoside analogues has been achieved by the three-component coupling reaction of sugar alkynes, pyridines and α-bromo carbonyl compounds in one pot. The corresponding products are obtained in good to excellent yields. 49 examples have been given. The synthetic method is convenient, practical and efficient. It is suitable for various substrates including structurally diversified sugar alkynes with sensitive groups. The sugar alkynes include pyranosides, furanosides, and acyclic sugars. A plausible mechanism for the formation of indolizine C-nucleoside analogues has been elucidated.

摘要

新型吲哚嗪 C-核苷类似物的合成为三组分一锅法,由糖炔、吡啶和α-溴代羰基化合物反应而成。相应产物的产率良好至优秀。给出了 49 个实例。该合成方法方便、实用、高效。它适用于各种底物,包括具有敏感基团的结构多样化的糖炔。糖炔包括吡喃糖苷、呋喃糖苷和无环糖。已经阐明了形成吲哚嗪 C-核苷类似物的合理机制。

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