Facile Synthesis of Novel Benzoylthiophene C-Nucleoside Analogues via Coupling of Sugar Alkynes, Aroyl Chlorides, and 1,4-Dithiane-2,5-diol
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Published:2020-01-30
Issue:09
Volume:52
Page:1435-1443
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ISSN:0039-7881
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Container-title:Synthesis
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language:en
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Short-container-title:Synthesis
Author:
Liu Hong1,
Zhang Fuyi1,
Luo Yang1,
Gao Fei1,
Zhao Yufen12
Affiliation:
1. College of Chemistry, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University
2. Institute of Drug Discovery Technology, Ningbo University
Abstract
Concise synthesis of novel benzoylthiophene C-nucleoside analogues has been achieved by the reaction of various terminal sugar alkynes with substituted benzoyl chlorides and 1,4-dithiane-2,5-diol, and subsequent dilute HCl-promoted dehydration in one pot. The sugar alkynes include pyranosides, furanosides, and acyclic sugar. The benzoyl chloride has various substituents. Twenty-eight examples are given. The desired products are obtained in 70–89% yields, and the mechanism has been clarified by isolation of the intermediate.
Funder
National Natural Science Foundation of China
Publisher
Georg Thieme Verlag KG
Subject
Organic Chemistry,Catalysis
Cited by
1 articles.
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