Predictably Selective (sp3)C-O Bond Formation through Copper Catalyzed Dehydrogenative Coupling: Facile Synthesis of Dihydro-oxazinone Derivatives was written by Modak, Atanu;Dutta, Uttam;Kancherla, Rajesh;Maity, Soham;Bhadra, Mohitosh;Mobin, Shaikh M.;Maiti, Debabrata. And the article was included in Organic Letters in 2014.COA of Formula: C11H15NO2 This article mentions the following:
An intramol. dehydrogenative (sp3)C-O bond formation in salicylamides can be initiated by an active Cu/O2 species to generate pharmaceutically relevant dihydrooxazinones. E.g., in presence of CuCl2 and pyridine in m-xylene at 130 °C, dehydrogenative coupling of salicylamide derivative (I) gave 90% 2H-benz[e][1,3]oxazin-4(3H)-one derivative (II). Exptl. findings suggest that stereoelectronic parameters in both coupling partners are controlling factors for site selectivity in bond formation. Mechanistic investigations including isotope labeling and kinetic studies helped us to propose a catalytic cycle. The method provides a convenient synthesis of an investigational new medicine CX-614, which has potential in finding treatment for Parkinson’s and Alzheimer’s diseases. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2COA of Formula: C11H15NO2).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.COA of Formula: C11H15NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics