Synthetic applications of nitrogen-nitrogen linked heterocycles. Part 4. The reaction between 1-pyridinio-4-pyridone cations and cyanide ion: mechanism of cyanopyridine formation, and a regioselective synthesis of 4-cyanopyridines was written by Leung, Christopher W. F.;Sammes, Michael P.;Katritzky, Alan R.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1979.Application In Synthesis of 4-Methylpicolinonitrile This article mentions the following:
Treating pyridiniopyridones I (R = H, R1 = H, alkyl) with aqueous NaCN gave mixtures of 2- and 4-cyanopyridines, favored by high and low CN– concentrations, resp. Small amounts of 1,4-dihydro-4-cyano adducts were also obtained at low CN– concentrations E.g., an 8.73:1 ratio of CN– and I (R = R1 = H) gave 37% 2-cyanopyridine (II) and 17% 4-cyanopyridine (III), whereas a 2.47:1 ratio of starting materials gave 7% II and 51% III. I (R = Me, R1 = H, alkyl) gave high yields of 1,4-dihydro-4-cyano adducts. E.g., I (R = Me, R1 = H) gave 78% IV (R2 = H) and IV (R2 = Me), the IV mixture decomposed quant. on heating to a mixture of III and 2,6-dimethyl-4-pyridone. 2-Cyanopyridines were probably formed via 1,2-dihydro-2-cyano adducts. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Application In Synthesis of 4-Methylpicolinonitrile).
4-Methylpicolinonitrile (cas: 1620-76-4) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application In Synthesis of 4-Methylpicolinonitrile