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

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.

Key words

carbodiimide - N-acyl chloroformamidine - 1,1-diaminoethylene - amidine - urea

• References


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