Reactions of Phenylacetylenes with Azomethines -Syntheses of 3 Phenyl 2 propynylamine and Quinoline Derivatives-

Abstract

Phenylacetylenes E 1 reacted with aliphatic azomethines C 2 J in the presence of a catalytic amount of zinc chloride, yielding 3-phenyl-2-propynylatnines C 3D. The reaction of p-nitrophenylacetylene with N-isobutylidene-t-butylamine gave, in addition to propynylamine 13 k, trans-2, 2-dimethy1-4- (p-nitrophenyl) -3-butenal C 6 J after treatment with acid. Phenylacetylenes C 1 reacted with N-benzylideneanilines C 7 J under catalytic influence of zinc ( chloride to give quinoline derivatives C10). Analogously, 2, 4-diphenylbenzo[h]quinoline C.12 was obtained from phenylacetylene and N-benzylidene-1-naphthylamine. The present method offers a facile synthetic route to a variety of 2, 4-diphenylquinoline derivatives.