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

Coburn M. D. | Zendy; Buntain G. A. | Zendy; Harris B. W. | Zendy; Hiskey M. A. | Zendy; Lee K.Y. | Zendy; Ott D. G. | Zendy

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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

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.

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