C(2)-Functionalization of 1-substituted imidazoles with Cyanoacetylene (cas 1070-71-9)s and aromatic or heteroaromatic aldehydes

Add time:07/27/2019    Source:sciencedirect.com

Substituted imidazoles (substituents are Me, Et, i-Bu, n-Hexyl, (CH2)2S–Bu-n, Ph, Bn) react smoothly (room temperature, without catalyst and solvent) with cyanoacetylenes (3-phenyl-2-propynenitrile and 4-(1-butoxyethoxy)-4-methyl-2-pentynenitrile) and aromatic or heteroaromatic aldehydes (benzaldehyde, 4-CN-benzaldehyde, pyridine-3-aldehyde) to give 3-(2-imidazolyl)-3-aryl-2-acylpropanenitriles, a hitherto unknown family of functionalized imidazole derivatives, in up to 62% yield. This three-component manifold represents a novel C(2)-functionalization of the imidazole nucleus involving zwitterionic, carbene and enol ether intermediates. Unlike the analogous reaction with aliphatic aldehydes, which gives enol ethers, in this case the latter undergo the further rearrangement to 3-(2-imidazolyl)-3-aryl-2-acylpropanenitriles.

We also recommend Trading Suppliers and Manufacturers of Cyanoacetylene (cas 1070-71-9). Pls Click Website Link as below: cas 1070-71-9 suppliers

Prev:The microwave spectra of the weakly bound complex between carbon monoxide and Cyanoacetylene (cas 1070-71-9), OC HCCCN
Next:An experimental study of the reactivity of CN− and C3N− anions with Cyanoacetylene (cas 1070-71-9) (HC3N))