Marek T. Cegla

Regioselective additions of grignard and lithium reagents to 2-[(benzylidene)aminoi]benzonitrile and 2-[(diphenylmethylene)amino]benzonitrile

Abstract Phenylmagnesium bromide and methylmagnesium bromide in tetrahydrofuran undergo a regioselective addition to the cyano group of the two title compounds. Phenyllithium and methyllithium add selectively to the azomethine portion of 2-[(benzylidene)amino]benzonitrile, but to the cyano group of 2-[(diphenylmethylene)amino]benzonitrile. These addition reactions are utilized in the synthesis of quinazoline derivatives.

Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides

Abstract Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiffs bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta -substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.