An improved synthesis of 3, 6??diamino??1, 2, 4, 5??tetrazine. II. From triaminoguanidine and 2, 4??pentanedione

MD Coburn, GA Buntain, BW Harris…

Index: Coburn, M.D.; Buntain, G.A.; Harris, B.W.; Hiskey, M.A.; Lee, K.-Y.; Ott, D.G. Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 8 p. 2049 - 2050

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Citation Number: 109

Abstract

Abstract A new synthesis for the title compound that gives an 80% overall yield was developed. Treatment of triaminoguanidine monohydrochloride (1) with 2, 4-pentanedione (2) gave 3, 6-bis (3, 5-dimethylpyrazol-1-yl)-1, 2-dihydro-1, 2, 4, 5-tetrazine (3) in 80–85% yield. Oxidation of 3 with nitric oxide or nitrogen dioxide to 3, 6-bis (3, 5-dimethyylpyrazol-1- yl)-1, 2, 4, 5-tetrazine (4) followed by ammonolysis of 4 gave 3, 6-diamino-1, 2, 4, 5- ...