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Synthesis of macrobicyclic compounds containing diazacrown ether moieties and ortho-aminobenzylic spacers

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Abstract

N,N´-Bis(2-bromobenzyl) diaza-15-crown-5 and -diaza-18-crown-6 ethers were obtained in high yields. Palladium-catalyzed amination of these compounds with equimolar amounts of linear polyamines and oxadiamines afforded a large number of macrobicyclic compounds. It was found that the structure of starting compounds is crucial for the formation of the target cryptands and that their yields can substantially be increased by using larger catalyst loadings.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 3 build., 1 Leninskie Gory, 119991, Moscow, Russian Federation

    N. M. Chernichenko, A. D. Averin & I. P. Beletskaya

  2. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 4 build., 31 Leninsky prosp., 119991, Moscow, Russian Federation

    A. D. Averin, A. K. Buryak & I. P. Beletskaya

Authors
  1. N. M. Chernichenko
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  2. A. D. Averin
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  3. A. K. Buryak
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  4. I. P. Beletskaya
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Corresponding author

Correspondence to A. D. Averin.

Additional information

Based on the materials of the III International Scientific Conference “New Research Areas in Heterocyclic Chemistry” (September 17–21, 2013, Pyatigorsk, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2056–2063, September, 2014.

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Chernichenko, N.M., Averin, A.D., Buryak, A.K. et al. Synthesis of macrobicyclic compounds containing diazacrown ether moieties and ortho-aminobenzylic spacers. Russ Chem Bull 63, 2056–2063 (2014). https://doi.org/10.1007/s11172-014-0700-x

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  • DOI: https://doi.org/10.1007/s11172-014-0700-x

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