Efficient Synthesis of α-Ketoamides via 2-Acyl-5-aminooxazoles by Reacting Acyl Chlorides and α-Isocyanoacetamides

Efficient Synthesis of α-Ketoamides via 2-Acyl-5-aminooxazoles by Reacting Acyl Chlorides and α-Isocyanoacetamides

Acyl chlorides and α-isocyanoacetamides undergo an efficient reaction in dichloromethane in the presence of triethylamine to give 2-acyl-5-aminooxazoles. Subsequent acid hydrolysis of the 5-aminooxazole moiety leads to α-ketoamides in good overall yields.

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Veröffentlicht in:Organic letters 2010-02, Vol.12 (4), p.820-823
Hauptverfasser: Mossetti, Riccardo, Pirali, Tracey, Tron, Gian Cesare, Zhu, Jieping
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemical synthesis
Amides - chemistry
Catalysis
Chemical Sciences
Hydrocarbons, Chlorinated - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Nitriles - chemistry
Organic chemistry
Stereoisomerism
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Zusammenfassung:Acyl chlorides and α-isocyanoacetamides undergo an efficient reaction in dichloromethane in the presence of triethylamine to give 2-acyl-5-aminooxazoles. Subsequent acid hydrolysis of the 5-aminooxazole moiety leads to α-ketoamides in good overall yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902894p