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Issue 31, 2012
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Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides

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Abstract

The one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro-imidazolidindione intermediate. Acyl dichlorides have a dual function: to serve as the third component and to activate carbodiimides. In sharp contrast, the AlMe3-catalyzed sequential reaction from the same substrates gives the isomer.

Graphical abstract: Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides

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Publication details

The article was received on 26 Apr 2012, accepted on 06 Jun 2012 and first published on 14 Jun 2012


Article type: Communication
DOI: 10.1039/C2OB25799H
Citation: Org. Biomol. Chem., 2012,10, 6266-6270
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    Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides

    F. Zhao, Y. Wang, W. Zhang and Z. Xi, Org. Biomol. Chem., 2012, 10, 6266
    DOI: 10.1039/C2OB25799H

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