SYNTHESIS AND TRANSFORMATIONS OF CYANOMETHYL-1,2,4,5-TETRAZINES

Authors

  • С. Г. Толщина I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Р. И. Ишметова I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Н. К. Игнатенко I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • А. В. Коротина I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • П. А. Слепухин I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Г. Л. Русинов I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • В. Н. Чарушин I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/558

Keywords:

CH acids, cyanomethyltetrazine anions, ethyl cyanoacetate, 3, 6-dihetaryl-1, 2, 4, 5-tetrazines, 1, 3-indanedione, malonodinitrile, pyrrolo[1, 2-b][1, 5]tetrazines, tetrazine coordination compounds, nucleophilic substitution

Abstract

Derivatives of s-tetrazine containing malonodinitrile, ethyl cyanoacetate, and 1,3-indanedione fragments were synthesized by the nucleophilic substitution of heterocyclic groups in 3,6-diazolyl-1,2,4,5-tetrazines. Coordination compounds of the cyanomethyltetrazine anion with Cu+, Mn2+, and the tetrathiafulvalene radical cation were obtained, and their structures were determined. A transformation of cyanomethyltetrazines to pyrrolo[1,2-b][1,2,4,5]tetrazines catalyzed by metal cations was discovered.

Authors: S. G. Tolshchina, R. I. Ishmetova, N. K. Ignatenko, A. V. Korotina, P. A. Slepukhin, G. L. Rusinov, and V. N. Charushin

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (4), pp 604-617

http://link.springer.com/article/10.1007/s10593-013-1288-z

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Published

2013-05-02

Issue

No. 4 (2013)

Section

Original Papers