139259-72-6Relevant academic research and scientific papers
Rh(III)-Catalyzed C-H Amidation of Arenes with N-Methoxyamide as an Amidating Reagent
Ju, Guodong,Li, Guobao,Qian, Guanwen,Zhang, Jingyu,Zhao, Yingsheng
, p. 7333 - 7336 (2019/10/08)
The Rh(III)-catalyzed amidation of C(sp2)-H bonds has been reported by employing the N-methoxyamide as a novel amino source. An excellent level of functional group tolerance can be achieved when N-methoxyamide derivatives are used as the amidating reagents. Importantly, several known bioactive compounds such as Aminalon, Pregabalin, Gabapentin, and Probenecid can be transformed to effective amidating reagents, as a way to facilitate the development of new bioactive molecules.
A Direct Approach to Decoration of Bioactive Compounds via C-H Amination Reaction
Ju, Guodong,Yuan, Chunchen,Wang, Dongjie,Zhang, Jingyu,Zhao, Yingsheng
supporting information, p. 9852 - 9855 (2019/12/24)
The development of new methods to achieve the direct synthesis of bioactive organic molecules is always an important topic in organic synthesis. We hereby demonstrate that N-methoxyamide is an excellent amino source in the iridium-catalyzed intermolecular C-H amination reaction. The linkage of two bioactive organic molecules can be well achieved with this new protocol. More than 20 examples of decorated bioactive compounds were reported, which can facilitate the discovery of new bioactive molecules.
Reactive Intermediates from the Solvolysis of Mutagenic O-Alkyl N-Acetoxybenzohydroxamates
Bonin, Antonio M.,Glover, Stephen A.,Hammond, Gerard P.
, p. 1173 - 1180 (2007/10/02)
Mutagenic O-(para-substituted benzyl) N-acetoxybenzohydroxamates undergo acid-catalysed solvolysis in aqueous acetonitrile but three is a change in mechanism from AA11 to E1 on going from para electron-withdrawing substituents to para +M electron-donating groups.The former permit the formation of a discrete nitrenium ion intermediate whereas the latter promote a concerted elimination of a resonance stabilized benzyl carbocation.
Evidence for the Formation of Nitrenium Ions in the Acid-catalysed Solvolysis of Mutagenic N-Acetoxy-N-Alkoxybenzamides
Campbell, John J.,Glover, Stephen A.,Hammond, Gerard P.,Rowbottom, Colleen A.
, p. 2067 - 2080 (2007/10/02)
In aqueous acetonitrile, N-acetoxy-N-alkoxybenzamides undergo acid-catalysed solvolysis by the AAl1 mechanism to give acetic acid and nitrenium ions.This is indicated by an inverse dependence of the acid-independent rate constant, kH, upon the activity of water, a solvent kinetic isotope effect of 0.44 and positive Σ(excit.) values.In addition, relief of steric compression at the nitrogen enhances the rate of solvolysis.Hammett correlations with ?+ substituent constants were found for the rates of solvolysis of para-substituted-N-acetoxy-N-butoxybenzamides and N-acetoxy-N-(para-substituted benzyloxy) benzamides.This fact and the low ρ-values of -1.35 and -1.56, respectively, are indicative of a strong build-up of positive charge in the transition state which has both nitrenium ion and oxonium ion character and is in accordance with computed molecular-orbital properties of N-alkoxynitrenium ions.Greater levels of mutagenicity have been measured for those compounds which are more readily solvolysed to nitrenium ions.
