One-Pot Synthesis of N,N,N′,N′-Tetrasubstituted Ureas and Oxomalonamides by Oxidative Carbonylation of Lithium Amides at Atmospheric Pressure

Norma S. Nudelman; Elizabeth S. Lewkowicz; Daniel G. Pérez

doi:10.1055/s-1990-27053

Synthesis 1990; 1990(10): 917-920
DOI: 10.1055/s-1990-27053

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One-Pot Synthesis of N,N,N′,N′-Tetrasubstituted Ureas and Oxomalonamides by Oxidative Carbonylation of Lithium Amides at Atmospheric Pressure

Norma S. Nudelman^* , Elizabeth S. Lewkowicz, Daniel G. Pérez

^*Departamento de Química Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pab.II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina

Abstract

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N,N,N′,N′-tetrasubstituted ureas have been obtained in good yields by reaction of lithium aliphatic amides in tetrahydrofuran solution with carbon monoxide under mild conditions (0°C, 1013 mbar) followed by treatment with oxygen prior to work up. N,N,N′,N′- tetrasubstituted oxomalonamides (oxopropanediamides) can be obtained under similar reaction conditions by carrying out the reaction in the presence of known amounts of the pure amine. Besides being an useful synthetic method, the present studies afford new evidence of the mechanism of the reaction.

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