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    Tetrazine is an unstable compound that consists of a six-membered aromatic ring containing four nitrogen atoms with the molecular formula C2H2N4. The name tetrazine is used in the nomenclature of derivatives of this compound. Three core-ring isomers exist: 1,2,3,4-tetrazines, 1,2,3,5-tetrazines and 1,2,4,5-tetrazines



1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stablized as the dioxide derivatives.


1,2,4,5-Tetrazines are very well known and myriad 3,6-disubstituted 1,2,4,5-tetrazines are known [1]. These materials are of use in the area of energetic chemistry.

The compound 3,6-di-2-pyridyl-1,2,4,5-tetrazine [2] has two pyridine substituents and is of importance as a reagent in Diels-Alder reactions. It reacts with norbornadiene in a sequence of one DA reactions and two retro-DA reactions to cyclopentadiene and a pyridazine with exchange of an acetylene unit:

With norbornadiene fused to an arene the reaction stops at an intermediary stage [3]

See also


  1. ^ (see United States Patent 6645325)
  2. ^ Datasheet: Link
  3. ^ π-Bond Screening in Benzonorbornadienes: The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di(2-pyridyl)-s-Tetrazine. Ronald N. Warrener and Peter A. Harrison Molecules 2001, 6, 353–369 Online Article
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tetrazine". A list of authors is available in Wikipedia.
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