Reaction of 2-chloro-6-hydroxy-5,5-dimethyl-5,6-dihydro-1H-pyridine-3,4,4-tricarbonitriles with methanol

Abstract

We previously reported [1] that tetracyanoethylene reacts with aldehydes in the presence of excess hydrohalic acid to give 5,5-dialkyl-2-halo-6-hydroxy-5,6-dihydro-1H-pyridine-3,4,4-tricarbonitriles like I. Molecules of the products contain a hemiaminal moiety and spatially close axial hydroxy and cyano groups. We believe that such structure should favor mild intramolecular hydrolysis of the cyano group by nucleophiles (by analogy with structurally related compounds [2, 3]), as well as replacement of the hydroxy group.