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

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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.

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References

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Rostov State University, 194/3 pr. Stachki, 33477, Rostov-on-Don, Russian Federation

    L. Yu. Ukhin, V. N. Komissarov, G. I. Orlova & G. S. Borodkin

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    S. V. Lindeman, V. N. Khrustalev & Yu. T. Struchkov

Authors
  1. L. Yu. Ukhin
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  2. V. N. Komissarov
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  3. G. I. Orlova
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  4. G. S. Borodkin
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  5. S. V. Lindeman
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  6. V. N. Khrustalev
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  7. Yu. T. Struchkov
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2236–2240, November. 1995.

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Ukhin, L.Y., Komissarov, V.N., Orlova, G.I. et al. O-Tosylaminobenzaldehyde aminals in the synthesis of 1,3-disubstituted propargylamines, derivatives of 3H-2-vinylidene-3-aminoindoline and quinoline. Russ Chem Bull 44, 2142–2146 (1995). https://doi.org/10.1007/BF00696721

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  • DOI: https://doi.org/10.1007/BF00696721

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