33609-38-0

Upstream product

• 589-09-3 N-allyl-N-phenylamine 
• 1309388-54-2 3-(4-methoxyphenyl)-4-methyl-1-phenylimidazolidin-2-one 
• 1309388-64-4 1-allyl-3-(4-methoxyphenyl)-1-phenylurea 
• 622-80-0 N-propylaniline 
• 55240-30-7 N-n-propyl-N-phenyl carbamoyl chloride 
• 103-71-9 phenyl isocyanate 
• 75-44-5 phosgene 
• 223600-50-8 1-(2-hydroxy-1-methyl-ethyl)-3-phenyl-urea 

Downstream Products

• 6499-72-5 N¹-phenylpropane-1,2-diamine 

Relevant academic research and scientific papers

Photocatalytic Intramolecular C-H Amination Using N-Oxyureas as Nitrene Precursors

Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.

Gold(I)-catalyzed intramolecular hydroamination of N-allylic N′-arylureas to form imidazolidin-2-ones

Treatment of N-allylic N′-arylureas with a catalytic 1:1 mixture of di-tert-butyl-o-biphenylphoshphine gold(I) chloride and silver hexafluorophosphate (1 mol%) in chloroform at room temperature led to 5-exo-hydroamination to form the corresponding imidazolidin-2-ones in excellent yield. In the case of N-allylic ureas that possessed an allylic alkyl, benzyloxymethyl, or acetoxymethyl substituent, gold(I)-catalyzed 5-exo-hydroamination leads to formation of the corresponding trans-3,4-disubstituted imidazolidin-2-ones in excellent yield with ≥50:1 diastereoselectivity.

Investigation of the Mitsunobu reaction of N-(2-hydroxyethyl)-N'- phenyl-ureas

The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN=NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.