Palladium‐Catalyzed Coupling of N‐Amino­azoles with 3‐Halo‐Substituted ­Quinolin‐2(1H)‐ones, Coumarins, Quin­oxalin‐2(1H)‐ones, and Chromenes. Issue 8 (3rd February 2015)

• Record Type: Journal Article
• Authors: Luong, Thi Thanh Huyen; Brachet, Etienne; Brion, Jean‐Daniel; Messaoudi, Samir; Alami, Mouâd
• Is Part Of: European journal of organic chemistry. Issue 8(2015)
• Page Start: 1771
• Page End: 1780
• Publication Date: 2015-02-03
• Subjects: Synthetic methods -- Cross‐cou­pling -- Heterocycles -- Palladium -- P ligands; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403501
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient and general palladium‐catalyzed coupling of 3‐bromoquinolin‐2(1 H )‐ones, 3‐bromocoumarins, 3‐chloroquinoxalin‐2(1 H )‐ones, and 3‐iodo‐2 H ‐chromenes with a variety of 1‐aminoazoles is described. The reaction proceeds cleanly in the presence of the Pd(OAc)2 /4, 5‐bis(diphenylphosphino)‐9, 9‐dimethylxanthene (Xantphos) catalytic system to provide the coupling products in good to excellent yields. Abstract : The Pd(OAc)2 /4, 5‐bis(diphenylphosphino)‐9, 9‐dimethylxanthene (Xantphos) system catalyzes the coupling of 1‐aminoazoles with 3‐halo‐substituted quinolin‐2(1 H )‐ones, coumarins, quinoxalin‐2(1 H )‐ones, and chromenes. This process is efficient with various 1‐aminoazoles such as 1‐amino‐substituted indoles, indazoles, benzimidazoles, and azaindoles to give 3‐ N ‐substituted aminoazoles in good yields.