Modulating the Reactivity of α-Isocyanoacetates: Multicomponent Synthesis of 5-Methoxyoxazoles and Furopyrrolones

• Published in: Angewandte Chemie (International ed.) Vol. 46; no. 14; pp. 2485 - 2488
• Main Authors: Bonne, Damien, Dekhane, Mouloud, Zhu, Jieping
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.01.2007; WILEY‐VCH Verlag; Wiley; Wiley-VCH Verlag
• Subjects: Acetates - chemistry; Biochemistry, Molecular Biology; Chemistry; Chemistry, Multidisciplinary; furopyrrolones; isocyanides; Life Sciences; multicomponent reactions; oxazoles; Oxazoles - chemical synthesis; Physical Sciences; Pyrroles - chemical synthesis; Science & Technology; Ugi reaction; multicomponent reactions; ORGANIC-SYNTHESIS; 3-COMPONENT SYNTHESIS; METALATED ISOCYANIDES; ACID; furopyrrolones; 2-IMIDAZOLINES; Ugi reaction; COMPLEX-CATALYZED REACTION; UGI 4-COMPONENT; DOMINO PROCESS; CYCLOADDITION; isocyanides; oxazoles; PRIMARY AMINES
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200605005

A simple approach to complexity: The reactivity pattern of α‐isocyanoacetates can be tuned by modulating the acidity of the α CH bond(s) against the nucleophilicity of the conjugate base. The unique reactivity of the α‐(p‐nitrophenyl)‐α‐isocyanoacetate 1 was exploited in a three‐component synthesis of 5‐methoxyoxazoles 2 and four‐component synthesis of furopyrrolones 3. R1,R2,R3=alkyl, aryl, benzyl; R4=aryl.