Copper‐Catalyzed Tandem Amide N‐Arylation and Regioselective Cyclization of 2‐Alkynylbenzamides. Issue 3 (7th December 2015)

• Record Type: Journal Article
• Authors: Minami, Hideki; Sueda, Takuya; Okamoto, Noriko; Miwa, Yoshihisa; Ishikura, Minoru; Yanada, Reiko
• Is Part Of: European journal of organic chemistry. Issue 3(2016)
• Page Start: 541
• Page End: 548
• Publication Date: 2015-12-07
• Subjects: Heterocycles -- Domino reactions -- Copper -- Hypervalent compounds -- Cyclization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501330
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new approach to form iminoisocoumarins from readily available and stable 2‐alkynylbenzamides was developed by using a tandem copper‐catalyzed N ‐arylation and regioselective 6‐ endo ‐ dig cyclization in the presence of diaryliodonium salts, a copper catalyst, and 2, 6‐di‐ tert ‐butylpyridine. The arylation occurred at the nitrogen atom rather than the oxygen atom of the amide group, the alkynyl carbon, or the benzene ring of the benzamide. Cyclization occurred through a preferential nucleophilic attack by the oxygen rather than the nitrogen atom of the amide group to produce iminoisocoumarin derivatives in good to moderate yields. Abstract : A new approach to produce iminoisocoumarin derivatives in moderate yields was developed by using a tandem copper‐catalyzed N ‐arylation and regioselective 6‐ endo ‐ dig cyclization of 2‐alkynylbenzamides in the presence of diaryliodonium salts, a copper catalyst, and 2, 6‐di‐ tert ‐butylpyridine.