2002/02/16 by Pierre Janvier, Xiao‐Wen Sun, Hugues Bienaymé +1 · 2 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Multicomponent Synthesis of Heterocycles #Chemical Synthesis and Analysis #Synthesis and Characterization of Pyrroles
paper · doi:10.1021/ja017563a
openalex publication_date 2002/02/16 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/22
A novel multicomponent synthesis of 5-aminooxazole starting from simple and readily available inputs is described. Thus, simply heating a methanol solution of an aldehyde 3, an amine 4, and an alpha-isocyanoacetamide 5 provided the 5-aminooxazole (1) in good to excellent yield. The reaction of 1 with alpha,beta-unsaturated acyl chloride 13 lead to the formation of pyrrolo[3,4-b]pyridin-5-one (2) in a single operation. A triple domino sequence, acylation/IMDA/retro-Michael cycloreversion, is involved in this new scaffold-generating reaction. After the observation that ammonium chloride can significantly accelerate the oxazole formation in toluene, a one-pot four-component synthesis of 2 is developed.