Metal-Free Oxidative Amidation of 2‑Oxoaldehydes: A Facile Access to α‑Ketoamides

Metal-Free Oxidative Amidation of 2‑Oxoaldehydes: A Facile Access to α‑Ketoamides

A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a ce...

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Veröffentlicht in:Organic letters 2014-02, Vol.16 (4), p.1152-1155
Hauptverfasser: Mupparapu, Nagaraju, Khan, Shahnawaz, Battula, Satyanarayana, Kushwaha, Manoj, Gupta, Ajai Prakash, Ahmed, Qazi Naveed, Vishwakarma, Ram A
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Amides - chemical synthesis
Amides - chemistry
Dimethyl Sulfoxide - chemistry
Molecular Structure
Oxidation-Reduction
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Zusammenfassung:A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a central feature of reaction wherein C1-oxygen atom of α-ketoamides is finally derived from DMSO.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5000204