Construction of Isoquinolin‐1(2H)‐ones by Copper‐Catalyzed Tandem Reactions of 2‐(1‐Alkynyl)benzaldimines with Water. Issue 27 (20th August 2015)

• Record Type: Journal Article
• Authors: Zhang, Mingliang; Zhang, Hui‐Jun; Ruan, Wenqing; Wen, Ting‐Bin
• Is Part Of: European journal of organic chemistry. Issue 27(2015)
• Page Start: 5914
• Page End: 5918
• Publication Date: 2015-08-20
• Subjects: Homogeneous catalysis -- Copper -- Cyclization -- Oxidation -- Tandem reaction -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500908
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : The Cu(OAc)2 ‐catalyzed tandem reaction of 2‐(1‐alkynyl)benzaldimines with water for the synthesis of isoquinolin‐1(2 H )‐ones is developed. 4‐Halogen‐substituted isoquinolin‐1(2 H )‐ones can be obtained in good yields simply by including N ‐halosuccinimides (NXS) in the reaction system. Mechanistic studies are also undertaken.