A facile synthesis of unsymmetrical ureas

A facile and versatile method for the synthesis of unsymmetrical ureas from readily available reagents is reported. In the first step trifluoroethylchloroformate is reacted with a stoichiometric amount of a primary amine to give an intermediate trifluoroethyl carbamate. The addition of a second amin...

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Bibliographic Details
Published in:Tetrahedron 2011-05, Vol.67 (20), p.3619-3623
Main Authors: Bogolubsky, Andrey V., Ryabukhin, Sergey V., Pipko, Sergey E., Lukin, Oleg, Shivanyuk, Alexander, Mykytenko, Dmytro, Tolmachev, Andrey
Format: Article
Language:English
Subjects:
Aliphatic compounds
Amines
Chemistry
Combinatorial analysis
Exact sciences and technology
Libraries
Organic chemistry
Organofluorine compounds
Preparations and properties
Purity
Synthesis (chemistry)
Tetrahedrons
Trifluoroethyl carbamates
Trifluoroethylation
Trifluoroethylchloroformate
Ureas
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Summary:A facile and versatile method for the synthesis of unsymmetrical ureas from readily available reagents is reported. In the first step trifluoroethylchloroformate is reacted with a stoichiometric amount of a primary amine to give an intermediate trifluoroethyl carbamate. The addition of a second amine (primary or secondary) to the trifluoroethyl carbamate furnishes corresponding unsymmetrical ureas in 75–85% yield. A simple workup procedure, the high yields obtained, and the purity of the isolated products are suitable for the parallel synthesis of combinatorial libraries of unsymmetrical ureas with high structural and functional diversity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.03.101