Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

• Kohei Yamada,
• Naoto Kamimura and
• Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

• 2,4,5-trisubstituted oxazoles in good yields. Keywords: one-pot oxazole synthesis; Suzuki–Miyaura coupling; triazine; 5-(triazinyloxy)oxazole; trisubstituted oxazole; Introduction Oxazoles are found in numerous natural products and are used as a broad range of artificial compounds [1][2]. In

• synthesis of oxazolone from carboxylic acids and amino acids using a dehydrative condensing reagent, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM [19][20][21][22])[23]. Formation of 5-(triazinyloxy)oxazole is also reported to occur when an excess of DMT-MM was used. Recently

• trisubstituted oxazoles. Herein, we described an efficient method for the synthesis of trisubstituted oxazoles through a one-pot oxazole synthesis and subsequent Suzuki–Miyaura coupling. Results and Discussion The study was initiated with the preparation of the key intermediate, 5-(triazinyloxy)oxazole 3, from