Synthesis of symmetrical and unsymmetrical N-aryl-substituted cyclic ureas through copper(I) iodide catalyzed Goldberg-Buchwald-Nandakumar C-N coupling reactions
Journal
Synthesis
Journal Issue
9
Pages
1359-1366
Date Issued
2008
Author(s)
Abstract
The catalytic conditions of copper(I) iodide/potassium carbonate/trans-N, N′-dimethylcyclohexane-1,2-diamine, either in toluene at reflux temperature, or by heating neat at 150°C effectively promoted the C-N coupling of aryl bromides with cyclic ureas. By employing a protection- deprotection strategy, unsymmetrical diaryl-substituted cyclic ureas could also be synthesized. © Georg Thieme Verlag Stuttgart.
Subjects
Arylation; Copper; Cross-coupling; Heterocycles; Homogeneous catalysis
Other Subjects
Catalyst activity; Coupling agents; Deprotonation; Substitution reactions; Synthesis (chemical); Urea; Crosscoupling; Heterocycles; Homogeneous catalysis; Copper compounds; 1 [4 (methylsulfanyl)phenyl]imidazolidin 2 one; 1 tert butylimidazolidin 2 one; 1,3 bis(2 methoxyphenyl)imidazolidin 2 one; 1,3 bis(4 acetylphenyl)imidazolidin 2 one; 1,3 bis(4 cyanophenyl)imidazolidin 2 one; 1,3 bis(4 methoxyphenyl) 1,3 dihydro 2h benzimidazol 2 one; 1,3 bis(4 methoxyphenyl)imidazolidin 2 one; 1,3 bis(4 nitrophenyl) 1,3 dihydro 2h benzimidazol 2 one; 1,3 bis(4 nitrophenyl)imidazolidin 2 one; 1,3 bis[4 (ethoxycarbonyl)phenyl]imidazolidin 2 one; 1,3 bis[4 (methylsulfanyl)phenyl]imidazolidin 2 one; 1,3 di 1 naphthylimidazolidin 2 one; 1,3 di 2 pyridylimidazolidin 2 one; 1,3 di 4 tolylimidazolidin 2 one; 1,3 diaryl 1,3 dihydro 2h benzimidazol 2 one derivative; 1,3 diarylimidazolidin 2 one derivative; 1,3 diphenyl 1,3 di 2 pyridylurea; 1,3 diphenylimidazolidin 2 one; benzene derivative; cuprous ion; toluene; urea; article; arylation; catalysis; cross coupling reaction; drug structure; heating; methodology; stereochemistry; synthesis
Type
journal article