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AgOTf‐Catalyzed Electrophilic Cyclization of Triynols with NXS: Rapid Synthesis of Densely Trisubstituted Naphthalenes and Quinolines
Author(s) -
Chen Zhiyuan,
Jia Xuegong,
Ye Changqing,
Qiu Guanyinsheng,
Wu Jie
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201301186
Subject(s) - electrophile , synthon , moiety , chemistry , alkyne , naphthalene , trifluoromethanesulfonate , quinoline , catalysis , halogen , medicinal chemistry , functional group , combinatorial chemistry , organic chemistry , polymer , alkyl
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.