title: Generation of diverse 1-imidazolylisoquinolines via silver triflate-catalyzed reaction of 2-alkynylbenzaldoxime with imidazole.
abstract: Diverse 1-imidazolylisoquinolines are generated through a silver triflate-catalyzed cascade reaction of 2-alkynylbenzaldoxime with imidazole or benzoimidazole using parallel diversity-oriented synthesis. A small library of 1-imidazolylisoquinolines can be constructed efficiently under mild conditions. A plausible mechanism is proposed. We discovered that the presence of silver triflate and bromotrispyrrolidinophosphonium hexafluorophosphate (PyBroP) is essential for the reaction transformation. In the reaction process, treatment of 2-alkynylbenzaldoxime with silver triflate affords isoquinoline-N-oxide. Then, isoquinoline-N-oxide acts as a nucleophile to attack PyBroP to replace the bromide. Subsequently, an intermolecular nucleophilic addition of imidazole and further deprotonation take place to produce the desired 1-imidazolylisoquinolines. A range of great diversity could be easily introduced under the standard conditions during the reaction process.
authors.affiliation: Department of Chemistry, Nanchang University, Nanchang, Jiangxi, China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Xiao
authors.forename: Shengqing
authors.initials: S
authors.lastname: Ye
authors.forename: Danqing
authors.initials: D
authors.lastname: Zheng
authors.forename: Ling
authors.initials: L
authors.lastname: Zhang
authors.forename: Jie
authors.initials: J
authors.lastname: Wu
mesh_terms: D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*
chemical_list: D007093:Imidazoles; D007546:Isoquinolines; D008698:Mesylates; D010091:Oximes; C012077:trifluoromethanesulfonic acid