A Facile Synthesis of N,N-Bis[Formamidine]Ureas and Symmetrical N,N-Disubstituted Formamidines

D.   D.   Diaz; M.   G.   Finn

doi:10.2174/157017805774296957

Abstract

The reactivity of N,N-bis[(E)-dimethylamino)methylene]urea (1) with amines is described. Selective exchange of one of the N,N-dimethylamino fragments is possible with most of the benzylic amines tested, allowing the formation of 1-(alkylamino-methylene)-3-dimethylaminomethylene ureas as analytically pure precipitates in modest yields. Under acidic conditions, the urea fragment acts as leaving group leading the formation of symmetrical N,N-disubstituted formamidines.

Keywords: urea, formamidine, synthesis, amines, transamination reactions, acid, hydrolysis

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Letters in Organic Chemistry

Title: A Facile Synthesis of N,N-Bis[Formamidine]Ureas and Symmetrical N,N-Disubstituted Formamidines

Volume: 2 Issue: 7

Author(s): D. D. Diaz and M. G. Finn

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Keywords: urea, formamidine, synthesis, amines, transamination reactions, acid, hydrolysis

Abstract: The reactivity of N,N-bis[(E)-dimethylamino)methylene]urea (1) with amines is described. Selective exchange of one of the N,N-dimethylamino fragments is possible with most of the benzylic amines tested, allowing the formation of 1-(alkylamino-methylene)-3-dimethylaminomethylene ureas as analytically pure precipitates in modest yields. Under acidic conditions, the urea fragment acts as leaving group leading the formation of symmetrical N,N-disubstituted formamidines.

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Diaz D. D. and Finn G. M., A Facile Synthesis of N,N-Bis[Formamidine]Ureas and Symmetrical N,N-Disubstituted Formamidines, Letters in Organic Chemistry 2005; 2 (7) . https://dx.doi.org/10.2174/157017805774296957