82894-45-9Relevant academic research and scientific papers
Direct and practical synthesis of primary anilines through iron-catalyzed C-H bond amination
Legnani, Luca,Cerai, Gabriele Prina,Morandi, Bill
, p. 8162 - 8165 (2018/05/22)
The direct C-H amination of arenes is an important strategy to streamline the discovery and preparation of functional molecules. Herein, we report an operationally simple arene C-H amination reaction that, in contrast to most literature precedent, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II)-sulfate serves as a convenient catalyst for the transformation. The reaction tolerates a wide scope of arenes, including structurally complex drugs. Importantly, the arene substrates are used as limiting reagents in the transformation. This operationally simple transformation should considerably accelerate the discovery of medicines and functional molecules.
MAO inhibition by arylisopropylamines: The effect of oxygen substituents at the β-position
Osorio-Olivares, Mauricio,Rezende, Marcos Caroli,Sepulveda-Boza, Silvia,Cassels, Bruce K.,Fierro, Angelica
, p. 4055 - 4066 (2007/10/03)
Twenty-nine arylisopropylamines, substituted at the β-position of their side chain by an oxo, hydroxy, or methoxy group, were evaluated in vitro as MAO-A and MAO-B inhibitors. The oxo derivatives ('cathinones') were in general less active as MAO-A inhibitors than the corresponding arylisopropylamines, but exhibited an interesting MAO-B inhibiting activity, which was absent in the hydroxy, methoxy, and β-unsubstituted analogues. These results suggest that selective affinity for the two MAO isoforms in this family of compounds is modulated not only by the aryl substitution pattern but also by the side-chain substituents on the arylalkylamine scaffold.
A Reinvestigation of the Pictet-Gams Isoquinoline Synthesis. Part 2. Formation of Rearranged Isoquinolines: the Δ2-Oxazoline-Isoquinoline Transformation
Ardabilchi, Nasser,Fitton, Alan O.,Hadi, A. Hamid b. A.,Thompson, J. Robin
, p. 1710 - 1725 (2007/10/02)
Cyclisation of a series of 2-substituted 2-acylamino-1-arylalkan-1-ols using phosphorus pentaoxide in refluxing decalin is shown to lead to rearranged, i.e. 4-substituted, isoquinolines in addition to the anticipated 3-substituted isomers.The products arise largely via 5-phenyl-Δ2-oxazoline intermediates and the formation of the rearranged isoquionolines from these intermediates is fully discussed.The pathway is not substantially altered when 2-benzamido-1-methoxy-1-phenylalkanes are cyclised.
