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Synthesis 2013; 45(3): 347-354
DOI: 10.1055/s-0032-1316833
DOI: 10.1055/s-0032-1316833
paper
Synthesis, Characterization, and Reactivity of N-Acyl Chloroformamidines: Useful Building Blocks for the Construction of N-Acyl-Substituted 1,1-Diaminoethylenes, Amidines, Ureas, and Thioureas
Further Information
Publication History
Received: 23 October 2012
Accepted after revision: 03 December 2012
Publication Date:
12 December 2012 (online)
Abstract
The systematic synthesis of a series of N-acyl chloroformamidines is achieved by reaction of carbodiimides with acid chlorides; the structure of an N-acyl chloroformamidine was confirmed by X-ray diffraction. The reactivity of N-acyl chloroformamidines towards diethyl malonate, phenylethynyllithium, pentane-2,4-dione, methyl acetoacetate, water, 1,3-dimethylurea, 1,3-dimethylthiourea, and sodium hydrosulfide, resulted in unique protocols for the synthesis of N-acyl-substituted 1,1-diaminoethylenes, amidines, ureas, and thioureas, respectively. These results show that N-acyl chloroformamidines have a good ability to accept nucleophilic attack for the construction of useful N-containing compounds.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are spectroscopic data (1H and 13C NMR spectra for new compounds and X-ray data for compound 3a).
- Supporting Information
-
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Selected reviews of carbodiimide chemistry:
Selected examples of cycloaddition of carbodiimides:
Selected examples of addition of nucleophiles to carbodiimides:
For examples of rearrangement of carbodiimides, see:
For examples of carbodiimide metathesis:
1,1-Diaminoethene:
Amidines:
Ureas:
For the synthesis of N-acylureas, see: