TETRAZINE

'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

Contents

1,2,3,4-tetrazines

1,2,4,5-tetrazine

See also

References

1,2,3,4-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-tetrazine

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

★ 6-membered rings with three nitrogen atoms: triazines

★ 6-membered rings with two nitrogen atoms: diazines

★ Pyridine

References

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