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Journal of Carbohydrate Chemistry Volume 41, 2022 - Issue 1
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Research Articles

Facile synthesis of novel 3H-1,5-benzodiazepine-derived aryl C-glycosides by coupling of sugar alkynes, acyl chlorides and 1, 2-phenylenediamine

Qianxia Chena Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, ChinaView further author information
,
Xiang Zhoua Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, ChinaView further author information
,
Fen Hana Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, ChinaView further author information
,
Fuyi Zhanga Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, ChinaCorrespondence[email protected]
View further author information
&
Yufen Zhaoa Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, China;b Institute of Drug Discovery Technology, Ningbo University, Ningbo, ChinaView further author information
Pages 28-50 | Received 28 Dec 2021, Accepted 16 Feb 2022, Published online: 04 Mar 2022
 
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Abstract

Novel 3H-1,5-benzodiazepine-derived aryl C-glycosides were synthesized in good to excellent yields by the coupling of structurally diverse terminal sugar alkynes, aroyl chlorides and 1, 2-phenylenediamine. The protocol is general, mild and efficient. It was suitable for various terminal sugar alkynes and aroyl chlorides, with 37 selected examples. The sugar substrates include pyranosides, furanosides, and acyclic sugars with sensitive and bulky protecting groups. The aroyl chlorides contain electron-donating, electron-withdrawing and electron-neutral substituents.

Additional information

Funding

We gratefully acknowledge the National Natural Science Foundation of China [No. 21772180] for financial support.

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