O-Tosylaminobenzaldehyde aminals in the synthesis of 1,3-disubstituted propargylamines,derivatives of 3H-2-vinylidene-3-aminoindoline and quinoline |
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| Authors: | L Yu Ukhin V N Komissarov G I Orlova G S Borodkin S V Lindeman V N Khrustalev Yu T Struchkov |
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| Institution: | (1) Institute of Physical and Organic Chemistry, Rostov State University, 194/3 pr. Stachki, 33477 Rostov-on-Don, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation |
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| Abstract: | 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.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2236–2240, November. 1995. |
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| Keywords: | o-tosylaminobenzaldehyde aminals 3H-2-vinylidene-3-aminoindoline derivatives 1 3-disubstituted propargylamines quinoline derivatives X-ray diffraction study |
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