title: Synthesis of substituted mono- and diindole C-nucleoside analogues from sugar terminal alkynes by sequential sonogashira/heteroannulation reaction.
abstract: The synthesis of substituted mono- and diindole C-nucleoside analogues has been achieved in good to excellent yields by sequential Sonogashira coupling/NaAuCl4-catalyzed heteroannulation reactions of substituted 2-iodoanilines with various sugar terminal alkynes in one pot. The method is general, mild, and efficient and suitable for a wide range of sugar substrates, and 42 examples are given. The amino group of the substituted 2-iodoanilines is unprotected. The sugar terminal alkynes include furanosides, pyranosides, and acyclic glycosides with free hydroxyl groups, sensitive functional subtituents, and various protecting groups having different steric hindrance.
authors.affiliation: The College of Chemistry and Molecular Engineering, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University , Zhengzhou, 450001, China.
authors.forename: Fuyi
authors.initials: F
authors.lastname: Zhang
authors.forename: Delong
authors.initials: D
authors.lastname: Mu
authors.forename: Liming
authors.initials: L
authors.lastname: Wang
authors.forename: Pengfei
authors.initials: P
authors.lastname: Du
authors.forename: Fen
authors.initials: F
authors.lastname: Han
authors.forename: Yufen
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002241:Carbohydrates; D006027:Glycosides; D007211:Indoles; D009705:Nucleosides