A General Synthesis of Unsymmetrical Tetrasubstituted Ureas

Author:

Katritzky Alan R.1,Pleynet David P. M.1,Yang Baozhen1

Affiliation:

1. Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Reference33 articles.

1. Substituted Ureas. Methods of Synthesis and Applications

2. Antiviral and pharmacokinetic properties of C2 symmetric inhibitors of the human immunodeficiency virus type 1 protease

3. Discovery of a novel class of potent HIV-1 protease inhibitors containing the (R)-(hydroxyethyl)urea isostere

4. The most important of the wide variety of methods to prepare mono- di- and trisubstituted ureas1,5mostly fall into three main groups. In the first place, primary amines are reacted with carbonyl insertion compounds such as phosgene,5trisphosgene,6various carbonates,7-9S,S-dimethyl thiocarbonate,10andN,N‘-carbonyldiimidazole.11The second class comprises the reactions of primary amines with NCO equivalent compounds like carbamates,12-14formamides (in the presence of a ruthenium catalyst),15and most importantly isocyanates.5,16Thirdly, ureas have been prepared by the catalyzed carbonylation of amines using carbon monoxide17-20or carbon dioxide21,22in the presence of metal complexes, selenium,17phosphorus compounds,23,24andN,N‘-dicyclohexylcarbodiimide.25

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