59898-94-1Relevant academic research and scientific papers
Mapping out the Relative Influence of Hydrogen and Halogen Bonds in Crystal Structures of a Family of Amide-Substituted Pyridines
Abeysekera, Amila M.,Day, Victor W.,Sinha, Abhijeet S.,Aaker?y, Christer B.
, p. 7399 - 7410 (2020/11/03)
The simultaneous use of hydrogen bonds and halogen bonds in crystal engineering strategies has previously been employed in order to generate new solid forms with applications in e.g. pharmaceutical and agrochemical industries. Unfortunately, it is not eas
Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
supporting information, p. 482 - 487 (2019/01/04)
A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
A Cross-Coupling Approach to Amide Bond Formation from Esters
Ben Halima, Taoufik,Vandavasi, Jaya Kishore,Shkoor, Mohanad,Newman, Stephen G.
, p. 2176 - 2180 (2017/08/09)
A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C-O bond by oxidative addition with a Pd-NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic, and heterocyclic products are obtained. A range of activated esters are evaluated in the presence and absence of catalyst, demonstrating that the catalytic methodology substantially increases the types of electrophiles that can be utilized for amide bond formation in the absence of harsh bases.
Establishing supramolecular control over solid-state architectures: A simple mix and match strategy
Aakeroey, Christer B.,Panikkattu, Sheelu V.,Dehaven, Baillie,Desper, John
experimental part, p. 2579 - 2587 (2012/08/28)
With the help of robust principles of crystal engineering, it is possible to construct co-crystals where two or more different molecular entities coexist in the same crystalline lattice; the supramolecular assembly is driven by noncovalent interactions, most commonly by hydrogen bonds. We have synthesized two ditopic amide based ligands (N-(4-pyridin-2-yl)isonicotinamide) and (N-(3-pyridin-2-yl)nicotinamide) and systematically established their binding preferences when faced with aliphatic dicarboxylic acids with an odd and even number of carbon atoms. Each ligand was co-crystallized with four odd and four even-chain dicarboxylic acids, and 13/16 reactions produced crystals suitable for single-crystal structure determination. On the basis of these results, it is clear that carefully selected systems can be manipulated to produce assemblies in the solid state with very precise control over topology and dimensionality. These ligands can be made to produce either 0-D or 1-D architectures simply by fine-tuning the choice of co-crystallizing agent in the supramolecular synthesis. This mix-and-match strategy allows us to mimic the reliability and versatility of covalent synthesis, in terms of successfully preparing a target with predetermined connectivity and metrics.
