Efficient synthesis of alpha-ketoamides via 2-acyl-5-aminooxazoles by reacting acyl chlorides and alpha-isocyanoacetamides

Riccardo Mossetti; Tracey Pirali; Gian Cesare Tron; Jieping Zhu

doi:10.1021/ol902894p

Efficient synthesis of alpha-ketoamides via 2-acyl-5-aminooxazoles by reacting acyl chlorides and alpha-isocyanoacetamides

Org Lett. 2010 Feb 19;12(4):820-3. doi: 10.1021/ol902894p.

Authors

Riccardo Mossetti¹, Tracey Pirali, Gian Cesare Tron, Jieping Zhu

Affiliation

¹ Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università degli Studi del Piemonte Orientale A. Avogadro, Via Bovio 6, 28100 Novara, Italy.

PMID: 20088495
DOI: 10.1021/ol902894p

Abstract

Acyl chlorides and alpha-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 alpha-ketoamides in good overall yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Catalysis
Hydrocarbons, Chlorinated / chemistry*
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Structure
Nitriles / chemistry*
Stereoisomerism

Substances

Amides
Hydrocarbons, Chlorinated
Ketones
Nitriles