1,2,4,5-Tetrazine → 1,2,4,5-Tetrazine

Participants

Reaction Steps

A solution of 1,2,4,5-tetrazine (0.53 M in dichloromethane) was prepared by the method of H. C. van der Plas et al. (J. Heterocycl. Chem., 1987, 24, 545-548). (2-Fluoro-5-nitrophenylethynyl)trimethylsilane (8.8 g, 37.1 mmol) and 1,4-dioxane were added to a solution of 1,2,4,5-tetrazine (35 ml, 18.6 mmol, 0.53 M in dichloromethane). The dichloromethane was distilled off and the dioxane solution was stirred at reflux for 36 h. The solvent was removed to leave a brown oil. Purification by chromatography (silica gel, 0-1% MeOH/CH2Cl2) gave 4-(2-fluoro-5-nitrophenyl)-5-trimethylsilanylpyridazine as a brown oil: MS (ES+) m/z 292 [M+H]+ and 249 [M−3CH2]+.

Provenance & Evidence