o-Tosylaminobenzaldehyde aminals in the synthesis of 1,3-disubstituted propargylamines, derivatives of 3H-2-vinylidene-3-aminoindoline and quinoline

Article abstract of DOI:10.1007/BF00696721

o-Tosylaminobenzaldehyde aminals react with propargyl alcohol and its phenyl ether on heating in acetonitrile in the presence of CuI to yield 3H-2-vinylidene-3-aminoindoline derivatives.Analogous reactions with phenylacetylene and dimethylethynylcarbinol result in 1,3-disubstituted propargylamines.The possibility of using the latter compounds in synthesis of quinoline derivatives was shown: cyclization of 1-(o-tosylaminophenyl)-1-morpholino-3-phenylprop-2-yne in the presence of H2SO4 and KOH gave 2-phenylquinoline and 2-phenyl-4-morpholinoquinoline, respectively. 3H-2-Phenoxymethylvinylidene-3-morpholinoindoline was studied by X-ray diffraction spectroscopy. - Keywords: o-tosylaminobenzaldehyde; 3H-2-vinylidene-3-aminoindoline derivatives; 1,3-disubstituted propargylamines; quinoline derivatives; X-ray diffraction study.