title: Copper-catalyzed one-pot synthesis of 1,2,4-triazoles from nitriles and hydroxylamine.
abstract: A simple and efficient copper-catalyzed one-pot synthesis of substituted 1,2,4-triazoles through reactions of two nitriles with hydroxylamine has been developed. The protocol uses simple and readily available nitriles and hydroxylamine hydrochloride as the starting materials and inexpensive Cu(OAc)2 as the catalyst, and the corresponding 1,2,4-triazole derivatives are obtained in moderate to good yields. The reactions include sequential intermolecular addition of hydroxylamine to one nitrile to provide amidoxime, copper-catalyzed treatment of the amidoxime with another nitrile, and intramolecular dehydration/cyclization. This finding provides a new and useful strategy for synthesis of 1,2,4-triazole derivatives.
authors.affiliation: Institute of Fine Chemistry and Engineering, Henan Engineering Laboratory of Flame-Retardant and Functional Materials, College of Chemistry and Chemical Engineering, Henan University , Kaifeng 475004, P. R. China.
authors.forename: Hao
authors.initials: H
authors.lastname: Xu
authors.forename: Shuang
authors.initials: S
authors.lastname: Ma
authors.forename: Yuanqing
authors.initials: Y
authors.lastname: Xu
authors.forename: Longxiang
authors.initials: L
authors.lastname: Bian
authors.forename: Tao
authors.initials: T
authors.lastname: Ding
authors.forename: Xiaomin
authors.initials: X
authors.lastname: Fang
authors.forename: Wenkai
authors.initials: W
authors.lastname: Zhang
authors.forename: Yanrong
authors.initials: Y
authors.lastname: Ren
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D019811:Hydroxylamine / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009570:Nitriles; D014230:Triazoles; C045575:1,2,4-triazole; D019811:Hydroxylamine; D003300:Copper