4392-85-2Relevant academic research and scientific papers
C?H Cyanation of 6-Ring N-Containing Heteroaromatics
Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Johnson, Tarn C.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,MacCoss, Malcolm,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.,Dixon, Darren J.
supporting information, p. 14733 - 14737 (2017/10/07)
Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.
Convenient and rapid strategies towards 6-(hetero)aryl pyridylmethylamines: First catalytic issues
Requet, Alexandre,Yalgin, Hasret,Prim, Damien
supporting information, p. 1378 - 1382 (2015/03/04)
The convenient preparation of new pyridylmethylamines is described using a short two step sequence. The first step involved the straightforward microwave-assisted construction of 6-aryl and 6-heteroaryl pyridine scaffolds bearing carboxaldehyde and nitrile fragments. The pendant arm comprising a second nitrogen atom by mean of amine and oxazoline moieties is installed in the second step. Finally, a first entry towards catalytic activity is given. In this context, modification of the ligand pattern and steric crowding around the central pyridine ring is examined and led to modest to fair ee's in the construction of binaphthyl substrates.
