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Heterocyclization of 3-aminocamphor and 3-aminoisoborneol derivatives with cyclic β-diketones and formaldehyde. Synthesis of optically active 1,2,3,4-tetrahydroquinoline derivatives with terpene substituents

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Chemistry of Natural Compounds Aims and scope

Spirocyclic 1,2,3,4-tetrahydroquinoline derivatives were prepared in quantitative yield by three-component condensation of dimedone or Meldrum’s acid with formaldehyde and (1S,3R,4S)-1,7,7-trimethyl-3(arylamino)bicyclo[2.2.1]heptan-2-one or (1S,2S,3R,4S)-1,7,7-trimethyl-3-(arylamino)bicyclo[2.2.1]heptan2-ol.

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Acknowledgment

We thank P. A. Slepukhin of I. Ya. Postovskii Institute of Organic Chemistry, Ural Branch, RAS, for performing the XSA. The work was supported by the RF President (Program for Support of Leading Scientific Schools, Grant NSh-4028.2008.3) and the RFBR 08-03-90011 Bel_a.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 220072, Minsk, Ul. Surganova, 13, Belarus

    A. P. Kadutskii & N. G. Kozlov

  2. Institute of Chemistry, Komi Scientific Center, Ural Branch, Russian Academy of Sciences, 167982, Syktyvkar, Ul. Pervomaiskaya, 48, Russian Federation

    L. L. Frolova, I. N. Alekseev & A. V. Kuchin

Authors
  1. A. P. Kadutskii
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  2. N. G. Kozlov
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  3. L. L. Frolova
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  4. I. N. Alekseev
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  5. A. V. Kuchin
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Corresponding author

Correspondence to N. G. Kozlov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2012, pp. 367–372.

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Kadutskii, A.P., Kozlov, N.G., Frolova, L.L. et al. Heterocyclization of 3-aminocamphor and 3-aminoisoborneol derivatives with cyclic β-diketones and formaldehyde. Synthesis of optically active 1,2,3,4-tetrahydroquinoline derivatives with terpene substituents. Chem Nat Compd 48, 404–411 (2012). https://doi.org/10.1007/s10600-012-0261-x

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  • DOI: https://doi.org/10.1007/s10600-012-0261-x

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