93731-94-3Relevant articles and documents
Potent natural soluble epoxide hydrolase inhibitors from Pentadiplandra brazzeana Baillon: Synthesis, Quantification, and Measurement of Biological Activities In Vitro and In Vivo
Kitamura, Seiya,Morisseau, Christophe,Inceoglu, Bora,Kamita, Shizuo G.,De Nicola, Gina R.,Nyegue, Maximilienne,Hammock, Bruce D.
, (2015)
We describe here three urea-based soluble epoxide hydrolase (sEH) inhibitors from the root of the plant Pentadiplandra brazzeana. The concentration of these ureas in the root was quantified by LC-MS/MS, showing that 1, 3-bis (4-methoxybenzyl) urea (MMU) i
Amine-Responsive Disassembly of AuI–CuI Double Salts for Oxidative Carbonylation
Cao, Yanwei,Yang, Jian-Gong,Deng, Yi,Wang, Shengchun,Liu, Qi,Shen, Chaoren,Lu, Wei,Che, Chi-Ming,Chen, Yong,He, Lin
supporting information, p. 2080 - 2084 (2019/12/24)
A sensitive amine-responsive disassembly of self-assembled AuI-CuI double salts was observed and its utilization for the synergistic catalysis was enlightened. Investigation of the disassembly of [Au(NHC)2][CuI2] revealed the contribution of Cu-assisted ligand exchange of N-heterocyclic carbene (NHC) by amine in [Au(NHC)2]+ and the capacity of [CuI2]? on the oxidative step. By integrating the implicative information coded in the responsive behavior and inherent catalytic functions of d10 metal complexes, a catalyst for the oxidative carbonylation of amines was developed. The advantages of this method were clearly reflected on mild reaction conditions and the significantly expanded scope (51 examples); both primary and steric secondary amines can be employed as substrates. The cooperative reactivity from Au and Cu centers, as an indispensable prerequisite for the excellent catalytic performance, was validated in the synthesis of (un)symmetric ureas and carbamates.
Iron-catalyzed urea synthesis: Dehydrogenative coupling of methanol and amines
Lane, Elizabeth M.,Hazari, Nilay,Bernskoetter, Wesley H.
, p. 4003 - 4008 (2018/05/04)
Substituted ureas have numerous applications but their synthesis typically requires the use of highly toxic starting materials. Herein we describe the first base-metal catalyst for the selective synthesis of symmetric ureas via the dehydrogenative coupling of methanol with primary amines. Using a pincer supported iron catalyst, a range of ureas was generated with isolated yields of up to 80% (corresponding to a catalytic turnover of up to 160) and with H2 as the sole byproduct. Mechanistic studies indicate a stepwise pathway beginning with methanol dehydrogenation to give formaldehyde, which is trapped by amine to afford a formamide. The formamide is then dehydrogenated to produce a transient isocyanate, which reacts with another equivalent of amine to form a urea. These mechanistic insights enabled the development of an iron-catalyzed method for the synthesis of unsymmetric ureas from amides and amines.
