52447-50-4Relevant articles and documents
N-Benzylazacyclophane synthesis via aromatic Mannich reaction
Díaz-Oviedo, Christian,Quevedo, Rodolfo
, p. 6571 - 6574 (2014)
A new method for synthesizing phenolic N-benzylazacyclophanes starting from tyramine is presented here. Computational calculations showed that macrocyclization is favored by the formation of hydrogen bond-based templates; these templates are not affected by including benzyl groups in the nitrogen atom of the tyramine moiety. The results showed that N-benzyl groups with electron-donating substituents have more nucleophilic nitrogen atoms, thereby favoring macrocyclization, while electron-withdrawing groups favor polymerization.
A Base and Solvent-Free Ruthenium-Catalyzed Alkylation of Amines
Celaje, Jeff Joseph A.,Zhang, Xingyue,Zhang, Forrest,Kam, Lisa,Herron, Jessica R.,Williams, Travis J.
, p. 1136 - 1142 (2017/08/09)
A (pyridyl)phosphine-ligated ruthenium(II) catalyst is reported for the chemoselective benzylic N-alkylation of amines, via a hydrogen-borrowing mechanism. The catalyst operates under mild conditions, neat, and without a base or other additive. These conditions offer remarkable functional group compatibility for applications in organic synthesis, including reactions involving phenols and anilines, which are very difficult to achieve. Mechanistic studies suggest that, unlike other catalysts for this reaction, the redox steps are fast and reversible while imine formation is slow. We perceive that this is the origin of the selectivity realized with these reaction conditions.
A multivalent approach to the discovery of long-acting β2- adrenoceptor agonists for the treatment of asthma and COPD
Jacobsen, John R.,Choi, Seok Ki,Combs, Jesse,Fournier, Eric J.L.,Klein, Uwe,Pfeiffer, Juergen W.,Thomas, G. Roger,Yu, Cecile,Moran, Edmund J.
, p. 1213 - 1218 (2012/03/11)
A multivalent approach was applied to the design of long-acting inhaled β2-adrenoceptor agonists. A series of dimeric arylethanolamines based on the short acting β2-adrenoceptor agonist albuterol were prepared, varying the nature and length of the linker between the basic nitrogens. None of the C2-symmetric dimers demonstrated increased potency, however dimer 5j, derived from 4-phenethylamine, was found to have increased binding potency in vitro relative to the parent monomer. Optimization of this structure led to the identification of 22 (milveterol) which demonstrates high potency in vitro and long duration of action in a guinea pig model of bronchoprotection.
