Issue 0, 1972

Triazines and related products. Part X. A re-examination of the reaction between benzil and diaminoguanidine nitrate

Abstract

Benzil reacts with diaminoguanidine nitrate to yield the nitrate salt of benzil mono[(aminoamidino)hydrazone](2). The hydrazone (2) is unstable, and cyclises on melting or in solvents to 5,6-diphenyl-3-hydrazino-1,2,4-triazine (3). Diazotisation of the hydrazone (2) and of hydrazine (3) affords the same product, 6,7-diphenyltetrazolo-[1,5-b]-as-triazine (9) which decomposes in boiling secondary amines to yield substituted 3-amino-5,6-diphenyl-1,2,4-triazines and hydrazoic acid. Both the hydrazone (2) and the hydrazine (3) react with triethyl orthoformate or formic acid to give 6,7-diphenyltriazolo[4,3-b]-as-triazine (16), which was also prepared, unambiguously, from benzil and 3,4-diamino-1,2,4-triazole. Although conditions favourable for Dimroth rearrangement were employed, no such transformations were encountered in the reactions of the bicyclic systems (9) and (16).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 1221-1225

Triazines and related products. Part X. A re-examination of the reaction between benzil and diaminoguanidine nitrate

M. F. G. Stevens, J. Chem. Soc., Perkin Trans. 1, 1972, 1221 DOI: 10.1039/P19720001221

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