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An improved synthesis of 3,6‐diamino‐1,2,4,5‐tetrazine. II. From triaminoguanidine and 2,4‐pentanedione
Author(s) -
Coburn M. D.,
Buntain G. A.,
Harris B. W.,
Hiskey M. A.,
Lee K.Y.,
Ott D. G.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280844
Subject(s) - tetrazine , chemistry , yield (engineering) , medicinal chemistry , organic chemistry , nuclear chemistry , metallurgy , materials science
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‐tetrazine ( 5 ) in guantitatively yields.