4.1 Article

Synthesis and transformations of cyanomethyl-1,2,4,5-tetrazines

Journal

CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 49, Issue 4, Pages 604-617

Publisher

SPRINGER
DOI: 10.1007/s10593-013-1288-z

Keywords

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

Funding

  1. Russian Foundation for Basic Research [11-03-00545-a]
  2. Russian Academy of Sciences Programs [12-P-3-1030, 12-P-3-1020, 12-T-3-1025]
  3. Grants Council of the President of the Russian Federation [NSh-5505.2012.3]

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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.

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