title: AgOTf-catalyzed electrophilic cyclization of triynols with NXS: rapid synthesis of densely trisubstituted naphthalenes and quinolines.
abstract: A silver triflate-catalyzed electrophilic cyclization reaction of acyclic triynols with NXS (X=I, Br) under mild conditions is reported. Three reactive functional groups, such as a carbonyl group, an alkyne group, and a halogen, could be selectively installed at the C1, C2, and C3 positions to obtain the naphthalene and quinoline products, respectively. The obtained densely trisubstituted products could be further transformed into more complex aromatic products by manipulating the alkynyl moiety and the other two functional groups as synthons.
authors.affiliation: Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi 330022 (P.R. China). zchenjx@hotmail.com.
authors.forename: Zhiyuan
authors.initials: Z
authors.lastname: Chen
authors.forename: Xuegong
authors.initials: X
authors.lastname: Jia
authors.forename: Changqing
authors.initials: C
authors.lastname: Ye
authors.forename: Guanyinsheng
authors.initials: G
authors.lastname: Qiu
authors.forename: Jie
authors.initials: J
authors.lastname: Wu
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D001974:Bromosuccinimide / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry*; D013997:Time Factors
chemical_list: D000438:Alcohols; D000480:Alkynes; D008698:Mesylates; D009281:Naphthalenes; D011804:Quinolines; D013388:Succinimides; C008155:N-iodosuccinimide; C012077:trifluoromethanesulfonic acid; D001974:Bromosuccinimide
keywords: electrophilic cyclization; heterocycles; homogeneous catalysis; silver triflate; triynol