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1,3-dipolar cycloaddition of trimethylsilyl azide to propynals and dimerization of 1H-1,2,3-triazole-5-carbaldehydes to tricyclic bis-hemiaminals

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Abstract

Reactions of trimethylsilyl azide with 3-trimethylsilyl-2-propynal and 2-propynal were studied. X-Ray analysis of the molecular structure of 4-trimethylsilyl-1H-1,2,3-triazole-5-carbaldehyde showed that the carbonyl group appears in the s-cis conformation with respect to the double C=C bond in the heteroring. The effect of the temperature and polarity of the medium on the ability of 1H-1,2,3-triazole-5-carbaldehyde to undergo dimerization to tricyclic bis-hemiaminals was examined by IR and 1H NMR spectroscopy.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. M. Demina, P. S. Novopashin, G. I. Sarapulova, L. I. Larina & A. S. Medvedeva

  2. Institute of the Earth’s Crust, Siberian Division, Russian Academy of Sciences, ul. Lermontova, 128, Irkutsk, 664033, Russia

    A. S. Smolin

  3. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    V. S. Fundamenskii & A. A. Kashaev

Authors
  1. M. M. Demina
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  2. P. S. Novopashin
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  3. G. I. Sarapulova
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  4. L. I. Larina
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  5. A. S. Smolin
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  6. V. S. Fundamenskii
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  7. A. A. Kashaev
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  8. A. S. Medvedeva
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 12, 2004, pp. 1852–1857.

Original Russian Text Copyright © 2004 by Demina, Novopashin, Sarapulova, Larina, Smolin, Fundamenskii, Kashaev, Medvedeva.

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Demina, M.M., Novopashin, P.S., Sarapulova, G.I. et al. 1,3-dipolar cycloaddition of trimethylsilyl azide to propynals and dimerization of 1H-1,2,3-triazole-5-carbaldehydes to tricyclic bis-hemiaminals. Russ J Org Chem 40, 1804–1809 (2004). https://doi.org/10.1007/s11178-005-0103-4

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  • DOI: https://doi.org/10.1007/s11178-005-0103-4

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