O-TOSYLAMINOBENZALDEHYDE AMINALS IN THE SYNTHESIS OF 1,3-DISUBSTITUTED PROPARGYLAMINES, DERIVATIVES OF 3H-2-VINYLIDENE-3-AMINOINDOLINE AND QUINOLINE

o-Tosylaminobenzaldehyde aminals react with propargyl alcohol and its phenyl ether on heating in acetonitrile in the presence of CuI to yiel d 3H-2-vinylidene-3-aminoindoline derivatives. Analogous reactions wit h phenylacetylene and dimethylethynylcarbinol result in 1,3-disubstitu ted propargylamines. The possibility of using the latter compounds in synthesis of quinoline derivatives was shown: cyclization of o-tosylam inophenyl)-1-morpholin-3-phenylprop-2-yne in the presence of H2SO4 and KOH gave 2-phenylquinoline and 2-phenyl-4-morpholinoquinoline, respec tively. 3H-2-Phenoxymethylvinylidene-3-morphindoline was studied by X- ray diffraction spectroscopy.