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Construction of Isoquinolin‐1(2 H )‐ones by Copper‐Catalyzed Tandem Reactions of 2‐(1‐Alkynyl)benzaldimines with Water
Author(s) -
Zhang Mingliang,
Zhang HuiJun,
Ruan Wenqing,
Wen TingBin
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500908
Subject(s) - chemistry , tandem , regioselectivity , halogen , catalysis , intramolecular force , medicinal chemistry , copper , reaction conditions , cascade reaction , stereochemistry , organic chemistry , materials science , alkyl , composite material
The Cu(OAc) 2 ‐catalyzed tandem reaction of 2‐(1‐alkynyl)benzaldimines with water for the synthesis of isoquinolin‐1(2 H )‐ones was developed. Moreover, 4‐halogen‐substituted isoquinolin‐1(2 H )‐ones were obtained in good yields simply by including N ‐halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective intramolecular cyclization of 2‐(1‐alkynyl)benzaldimines to give the corresponding isoquinolinium intermediates.