Details

Autor(en) / Beteiligte

• Metelkina, E. L.

Titel

2-Nitroguanidine derivatives: XI. Reactions of N′-nitrohydrazinecarboximidamide and 2-methylidene-N′-nitrohydrazinecarboximidamide with glyoxal

Ist Teil von

• Russian journal of organic chemistry, 2008-04, Vol.44 (4), p.495-498

Ort / Verlag

Dordrecht: SP MAIK Nauka/Interperiodica

Erscheinungsjahr

2008

Quelle

SpringerLink

Beschreibungen/Notizen

• The reaction of glyoxal with N ′-nitrohydrazinecarboximidamide (1-amino-2-nitroguanidine) in the presence of sodium hydroxide at a molar ratio of 1 : 1 : 1 gave N ′-nitro-2-(2-oxoethylidene)hydrazinecarboximidamide as a mixture of syn and anti isomers, whereas at a reactant ratio of 1:2:2 N ′-nitro-2-[(5-nitroamino-2 H -1,2,4-triazol-3-yl)methyl]hydrazinecarboximidamide and 3-nitroamino-4,5-dihydro-1,2,4-triazin-5-ol were formed. N ′-Nitro-2-(2-oxoethylidene)hydrazinecarboximidamide reacted with N ′-nitrohydrazinecarboximidamide in boiling ethanol to give N ′-nitro-2-[(5-nitroamino-2 H -1,2,4-triazol-3-yl)methyl]hydrazinecarboximidamide, while in glacial acetic acid 2,2′-(ethane-1,2-diylidene)bis( N ′-nitrohydrazinecarboximidamide) was obtained. The latter was also formed in the reaction of glyoxal with N ′-nitrohydrazinecarboximidamide in acetic acid at room temperature. The reaction of 2-methylidene- N ′-nitrohydrazinecarboximidamide with glyoxal led to the formation of 3-nitroimino-2,3,4-5-tetrahydro-1,2,4-triazine-5-carbaldehyde or 1-(methylideneamino)-2-(nitroimino)imidazolidine-4,5-diol, depending on the conditions.