Tetrazine
Class of chemical compounds
From Wikipedia, the free encyclopedia
Tetrazine is a 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, also known as v-tetrazines, as-tetrazines and s-tetrazines respectively.[1]
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.[2] These materials are of use[vague] in the area of energetic chemistry.[citation needed]
Heavily substituted tetrazines form the verdazyls, a family of stable radicals.[3]
Protected tetrazines are strong acetylene acceptors in Diels-Alder equilibria. For example, dipyridinyl 1,2,4,5-tetrazine abstracts acetylene from norbornadiene to cyclopentadiene and a pyridazine:[4] 1,2,4,5-tetrazines are widely used in bioorthogonal chemistry as part of inverse electron demand diels alder (IEDDA) reactions due to their biocompaibility and the degree of orthogonality they provide to other commonly used reactions such as click chemistry (CuAAC or SPAAC).[5][6]
With norbornadiene fused to an arene the reaction stops at an intermediary stage.[7]
See also
