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Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on 1,3-dipolar cycloaddition

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Abstract

Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on the 1,3-dipolar cycloaddition of substituted benzyl azides to tetra(propargyloxy)calix[4]arenes in the presence of copper iodide was carried out. The presence of the p-methoxybenzyl substituent in the triazole ring leads to a dramatic (more than tenfold) increase in the fluorescence of the corresponding macrocycle in a region of 290–310 nm.

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Authors and Affiliations

  1. Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    V. A. Burilov, I. S. Antipin & A. I. Konovalov

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    N. A. Epifanova, E. V. Popova, S. E. Solovieva, I. S. Antipin & A. I. Konovalov

  3. Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, 3 ul. Institutskaya, 630090, Novosibirsk, Russian Federation

    S. F. Vasilevsky

Authors
  1. V. A. Burilov
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  2. N. A. Epifanova
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  3. E. V. Popova
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  4. S. F. Vasilevsky
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  5. S. E. Solovieva
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  6. I. S. Antipin
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  7. A. I. Konovalov
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Correspondence to V. A. Burilov.

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Dedicated to the Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0766–0771, March, 2013.

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Burilov, V.A., Epifanova, N.A., Popova, E.V. et al. Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on 1,3-dipolar cycloaddition. Russ Chem Bull 62, 767–772 (2013). https://doi.org/10.1007/s11172-013-0104-3

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  • DOI: https://doi.org/10.1007/s11172-013-0104-3

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