Terminal bis-acetylenes derived from 1,2-bis(1H-tetrazol-5-yl)ethane
- Authors: Ishmetova R.I.1, Yachevskii D.S.1,2, Ignatenko N.K.1, Slepukhin P.A.1, Efimov I.V.2, Bakulev V.A.2, Rusinov G.L.1,2, Filyakova V.I.1, Charushin V.N.1,2
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Affiliations:
- I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
- Ural State Technical University named after the first President of Russia B. N. Yeltsin
- Issue: Vol 65, No 5 (2016)
- Pages: 1268-1271
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/238111
- DOI: https://doi.org/10.1007/s11172-016-1446-4
- ID: 238111
Cite item
Abstract
The N(1)—N(1), N(2)—N(2), and N(1)—N(2) regioisomers of 1,2-bis[(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane were first synthesized by alkylation of 1,2-bis(1H-tetrazol-5-yl)ethane with propargyl bromide. The peculiarities of the crystal structure of 1,2-bis[1-(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane were evaluated by X-ray diffraction analysis. This compound is readily underwent Cu-catalyzed [3+2] cycloaddition with p-tolyl azide, p-nitrophenyl azide, and benzyl azide to give heterocyclic assembles bearing 1,2,3-triazole and tetrazole cycles. Catalyst-free [3+2] cycloadditions of 1,2-bis[1-(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane and the mixtures of the N(1)—N(1), N(2)—N(2), N(1)—N(2) regioisomers with poly(glycidyl azide) oligomers resulted in 1,2,3-triazole cycles and crosslinking of the polymer chains.
About the authors
R. I. Ishmetova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: vif@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoy, Ekaterinburg, 620137
D. S. Yachevskii
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural State Technical University named after the first President of Russia B. N. Yeltsin
Email: vif@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoy, Ekaterinburg, 620137; 19 ul. Mira, Ekaterinburg, 620002
N. K. Ignatenko
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: vif@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoy, Ekaterinburg, 620137
P. A. Slepukhin
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: vif@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoy, Ekaterinburg, 620137
I. V. Efimov
Ural State Technical University named after the first President of Russia B. N. Yeltsin
Email: vif@ios.uran.ru
Russian Federation, 19 ul. Mira, Ekaterinburg, 620002
V. A. Bakulev
Ural State Technical University named after the first President of Russia B. N. Yeltsin
Email: vif@ios.uran.ru
Russian Federation, 19 ul. Mira, Ekaterinburg, 620002
G. L. Rusinov
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural State Technical University named after the first President of Russia B. N. Yeltsin
Email: vif@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoy, Ekaterinburg, 620137; 19 ul. Mira, Ekaterinburg, 620002
V. I. Filyakova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Author for correspondence.
Email: vif@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoy, Ekaterinburg, 620137
V. N. Charushin
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural State Technical University named after the first President of Russia B. N. Yeltsin
Email: vif@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoy, Ekaterinburg, 620137; 19 ul. Mira, Ekaterinburg, 620002