335459-64-8Relevant academic research and scientific papers
Ruthenium-Catalyzed Urea Synthesis by N-H Activation of Amines
Krishnakumar, Varadhan,Chatterjee, Basujit,Gunanathan, Chidambaram
supporting information, p. 7278 - 7284 (2017/06/23)
Activation of the N-H bond of amines by a ruthenium pincer complex operating via amine-amide metal-ligand cooperation is demonstrated. Catalytic formyl C-H activation of N,N-dimethylformamide (DMF) is observed in situ, which resulted in the formation of CO and dimethylamine. The scope of this new mode of bond activation is extended to the synthesis of urea derivatives from amines using DMF as a carbon monoxide (CO) surrogate. This catalytic protocol allows the synthesis of simple and functionalized urea derivatives with liberation of hydrogen, devoid of any stoichiometric activating reagents, and avoids the direct use of fatal CO. The catalytic carbonylation occurred at low temperature to provide the formamide; a formamide intermediate was isolated. The consecutive addition of different amines provided unsymmetrical urea compounds. The reactions are proposed to proceed via N-H activation of amines followed by CO insertion from DMF and with liberation of dihydrogen.
A simple conversion of amines into monosubstituted ureas in organic and aqueous solvents
Liu, Qi,Luedtke, Nathan W.,Tor, Yitzhak
, p. 1445 - 1447 (2007/10/03)
A versatile and highly efficient synthesis of monosubstituted ureas is described. The reaction of an amine with 4-nitrophenyl-N-benzylcarbamate, followed by hydrogenolysis, provides the corresponding urea in high yield and purity. This carbamate can also be employed for the derivatization of water-soluble polyamines (e.g. aminoglycoside antibiotics), while other reagents (e.g. benzylisocyanate) fail to give the desired products in any significant yield.
