53002-05-4Relevant academic research and scientific papers
Electrophilic tropylation of 2-aminopyridine
Yunnikova,Likhareva, Yu. E.,Akent’eva
, (2017)
Electrophilic tropylation of 2-aminopyridine afforded N-(cyclohepta-2,4,6-trien-1-yl)pyridin-2-amine. The product was tested for antibacterial activity against Staphylococcus aureus no. 906 and Candida albicans ATSS 24 433.
Copper(II) anilides in sp3 C-H amination
Jang, Eun Sil,McMullin, Claire L.,K??, Martina,Meyer, Karsten,Cundari, Thomas R.,Warren, Timothy H.
supporting information, p. 10930 - 10940 (2014/08/18)
We report a series of novel β-diketiminato copper(II) anilides [Cl2NN]Cu-NHAr that participate in C-H amination. Reaction of H 2NAr (Ar = 2,4,6-Cl3C6H2 (Ar Cl3), 3,5-(CF3)2C6H3 (ArF6), or 2-py) with the copper(II) t-butoxide complex [Cl 2NN]Cu-tOBu yields the corresponding copper(II) anilides [Cl2NN]Cu-NHAr. X-ray diffraction of these species reveal three different bonding modes for the anilido moiety: κ1-N in the trigonal [Cl2NN]Cu-NHArCl3 to dinuclear bridging in {[Cl2NN]Cu}2(μ-NHArF6)2 and κ2-N,N in the square planar [Cl2NN] Cu(κ2-NH-2-py). Magnetic data reveal a weak antiferromagnetic interaction through a π-stacking arrangement of [Cl2NN]Cu- NHArCl3; solution EPR data are consistent with monomeric species. Reaction of [Cl2NN]Cu-NHAr with hydrocarbons R-H (R-H = ethylbenzene and cyclohexane) reveals inefficient stoichiometric C-H amination with these copper(II) anilides. More rapid C-H amination takes place, however, when tBuOOtBu is used, which allows for HAA of R-H to occur from the tBuO? radical generated by reaction of [Cl 2NN]Cu and tBuOOtBu. The principal role of these copper(II) anilides [Cl2NN]Cu-NHAr is to capture the radical R? generated from HAA by tBuO? to give functionalized aniline R-NHAr, resulting in a novel amino variant of the Kharasch-Sosnovsky reaction.
Tritylamino aromatic heterocycles and related carbinols as blockers of Ca2+-activated potassium ion channels underlying neuronal hyperpolarization
Zunszain, Patricia A.,Shah, Mala M.,Miscony, Zena,Javadzadeh-Tabatabaie, Mazyar,Haylett, Dennis G.,Ganellin, C. Robin
, p. 159 - 166 (2007/10/03)
A series of novel aromatic tritylamino heterocycles has been synthesized and the compounds have been tested in comparison with clotrimazole for their ability to inhibit the slow afterhyperpolarization current (SlAHP) in cultured rat hippocampal pyramidal neurones. Some analogues of the clotrimazole metabolite, 2-chlorophenyl-diphenyl methanol, having different chlorination substitution in the triphenyl group have also been examined. Two compounds in particular, 3-[(2-chlorophenyl)diphenylmethylamino]pyridine (3a, UCL 1880) and 2-tritylaminothiazole (6, UCL 2027), are of special interest; they are effective blockers of the SlAHP (IC50 = 1.1-1.2 μM) and are much more selective than clotrimazole since they have less effect on the high voltage-activated Ca2+ current.
