3,6-Dipropyl-1,2,4,5-tetrazine synthesis

Yield:13717-92-5 92%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran;Reflux;

Steps:

Typical procedure for the synthesis of 3,6-disubstituted-1,2,4,5-tetrazines

General procedure: A mixture of 1,4-dihydro-3,6-disubstituted-1,4-bis(p-toluenesulfonyl)-1,2,4,5-tetrazines (0.500 mmol), TBAF 1.0 M solution in THF (0.550 ml, 0.550 mmol), and THF (5 ml) was refluxed until TLC monitored the full consumption of the starting material. Then, the reaction mixture was concentrated in vacuum to get a purple solid and washed with methanol (10 ml × 3), or directly filtered through a pad of silica gel to remove the catalyst and followed by rotary evaporation. For isolation of aliphatic 1,2,4,5-tetrazines, because of its highly volatile property, low-boiling petroleum ether or CH₂Cl₂ was used for column chromatography.

References:

Liu, Haixuan;Wei, Yunyang [Tetrahedron Letters,2013,vol. 54,# 35,p. 4645 - 4648] Location in patent:supporting information