Tetrazine is a compound that consists of a six-membered aromatic ring containing four nitrogen atoms with the molecular formula Carbon2Hydrogen2Nitrogen4. The name tetrazine is used in the nomenclature of derivatives of this compound. Three core-ring exist: 1,2,3,4-tetrazines, 1,2,3,5-tetrazines, and 1,2,4,5-tetrazines, also known as v-tetrazines, as-tetrazines and s-tetrazines respectively.
1,2,3,4-Tetrazines
1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stabilized as the dioxide derivatives.
1,2,4,5-Tetrazines
1,2,4,5-Tetrazines are very well known and myriad 3,6-disubstituted 1,2,4,5-tetrazines are known.
[(see United States Patent 6645325)] These materials are of use in the area of energetic chemistry.
Heavily substituted tetrazines form the , a family of .
Protected tetrazines are strong acetylene acceptors in Diels-Alder equilibria. For example, pyridine 1,2,4,5-tetrazine abstracts acetylene from norbornadiene to cyclopentadiene and a pyridazine:
With norbornadiene fused to an arene the reaction stops at an intermediary stage.
[ 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]
See also
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6-membered rings with one nitrogen atom: pyridine
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6-membered rings with two nitrogen atoms:
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6-membered rings with three nitrogen atoms:
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6-membered rings with five nitrogen atoms: pentazine
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6-membered rings with six nitrogen atoms: hexazine
