Melekhova, Anna A. published the artcileCopper(I)-Catalyzed 1,3-Dipolar Cycloaddition of Ketonitrones to Dialkylcyanamides: A Step toward Sustainable Generation of 2,3-Dihydro-1,2,4-oxadiazoles, HPLC of Formula: 2451-91-4, the publication is ACS Omega (2017), 2(4), 1380-1391, database is CAplus and MEDLINE.
CuI -catalyzed cycloaddition of the ketonitrones Ph2C=N+ (R’)O– (R’ = Me, CH2Ph) to the disubstituted cyanamides NCNR2 (R = Me2 , Et2 , (CH2)4 , (CH2)5 , (CH2)4O, C9H10, (CH2Ph)2 , Ph(Me)) gives corresponding 5-aminosubstituted 2,3-dihydro- 1,2,4-oxadiazoles (16 examples) in good to moderate yields. The reaction proceeds under mild conditions (CH2Cl2 , RT or 45 °C) and requires 10 mol% of [Cu(NCMe)4](BF4) as the catalyst. Somehow reduced yields are due to the individual properties of 2,3- dihydro-1,2,4-oxadiazoles, which easily undergo ring-opening via the N-O bond splitting. Results of the DFT calculations reveal that the cycloaddition of ketonitrones to CuI -bound cyanamides is a concerted process and the copper-catalyzed reaction is controlled by the predominant contribution of HOMOdipole-LUMOdipolarophile interaction (group I by the Sustmann’s classification). Metal-involving process is much more asynchronous and profitable from both kinetic and thermodn. viewpoints than the hypothetical metal-free reaction.
ACS Omega published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, HPLC of Formula: 2451-91-4.
Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics