O-Tosylaminobenzaldehyde aminals in the synthesis of 1,3-disubstituted propargylamines, derivatives of 3H-2-vinylidene-3-aminoindoline and quinoline
Russian Chemical Bulletin
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.
Ukhin, L. Yu; Komissarov, V. N.; Orlova, G. I.; Borodkin, G. S.; Lindeman, Sergey; Khrustalev, V. N.; and Struchkov, Yu T., "O-Tosylaminobenzaldehyde aminals in the synthesis of 1,3-disubstituted propargylamines, derivatives of 3H-2-vinylidene-3-aminoindoline and quinoline" (1995). Chemistry Faculty Research and Publications. 637.