Selective Nucleophilic Substitutions on Tetrazines.

Abstract

Other 6-membered heterocycles Other 6-membered heterocycles R 0670 Selective Nucleophilic Substitutions on Tetrazines. -The reaction of tetrazines such as (I) and (VI) bearing two leaving groups with different nucleophiles is studied. -(NOVAK, Z.; BOSTAI, B.; CSEKEI, M.; LOERINCZ, K.; KOTSCHY*, A.; Heterocycles 60 (2003) 12, 2653-2668; Dep. Gen. Inorg. Chem., Eoetvoes Lorand Univ., H-1518 Budapest, Hung.; Eng.) -Mais 14-180

Synthesis and characterization of 3,6-bis(1H-1,2,3,4-tetrazol-5-ylamino)-1,2,4,5-tetrazine (BTATz): Novel high-nitrogen content insensitive high energy material

“…The synthesis of precursors such as triaminoguanidine hydrochloride (TAG·HCl), 3,6-bis(3,5-dimethyl-pyrazol-1-yl)-1,2-dihydro-1,2,4,5-tetrazine (DHBPT) were as per the reported procedures [8][9][10][11].…”

“…Tetrazines have demonstrated powerful synthetic utility through their ability to participate in inverse electron demand Diels-Alder reactions [3] providing access to a wide range of heterocycles based high energy materials. Furthermore, tetrazines also possess high positive heats of formation and crystal densities, properties important for energetic materials applications [8][9][10][11].…”

“…Recently, considerable attention has been paid in the study of tetrazole and 1,2,4,5-tetrazine heterocycles [3][4][5][6][7][8][9][10][11][12][13][14]. Tetrazine moiety displayed unique and interesting characteristic properties.…”

Kinetic study on the aromatic nucleophilic substitution reaction of 3,6‐dichloro‐1,2,4,5‐tetrazine by biothiols

“…These reactions enable the preparation of new symmetrically and asymmetrically substituted derivatives, including products containing heteroatoms. The most common groups in tetrazines capable of leaving as anions are halogen atoms, the methylsulfanyl group, and the 3,5‐dimethylpyrazolyl fragment …”

“…One excellent example of what is mentioned earlier is the modification of 3,6‐dichloro‐1,2,4,5‐tetrazine (DCT) by the action of N‐nucleophiles and O‐nucleophiles,, which are often used to obtain tetrazine derivatives symmetrically and asymmetrically substituted with heteroatoms. In addition, reactions involving nucleophilic substitution of the halogen atoms in this tetrazine by the action of isobutyl mercaptan have also been reported . However, there are only a few works related to the ability of DCT to react with sulfhydryl groups of amino acids .…”