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- Title
2-nitroguanidine derivatives: VIII. Synthesis and cyclizations ofN'<sup>1</sup>,N'<sup>2</sup>-bis(N<sup>2</sup>- nitrocarbamimidoyl) dicarboxylic acid dihydrazides and ethyl [2-(N<sup>2</sup>-nitrocarbamimidoyl)-hydrazino](oxo)acetate.
- Authors
Metelkina, E.; Novikova, T.
- Abstract
New methods of synthesis ofN'1,N'2-bis(N2-nitrocarbamimidoyl) dicarboxylic acid dihydrazides and ethyl [2-(N2-nitrocarbamimidoyl)hydrazino](oxo)acetate from 1-methyl-2-nitro-1-nitrosoguanidine and dicarboxylic acid hydrazides were proposed. Cyclization ofN'1,N'2-bis(N2-nitrocarbamimidoyl) dihydrazides derived from malonic and succinic acids afforded the corresponding bis(3-nitroamino-1,2,4-triazol-5-yl)-alkanes, whileN'1,N'2-bis(N2-nitrocarbamimidoyl)oxalohydrazide gave rise to previously unknown 5,5'-bi-(3-nitroamino-1,2,4-triazole) salts. Heating of ethyl [2-(N2-nitrocarbamimidoyl)hydrazino](oxo)acetate in water in the presence of alkali metal hydroxides or carbonates resulted in intramolecular ring closure with formation of 5(3)-nitroamino-1,2,4-triazole-3(5)-carboxylic acid or ethyl 5(3)-nitroamino-1,2,4-triazole-3(5)-carboxylate, respectively. Depending on the conditions, ethyl [2-(N2-nitrocarbamimidoyl)hydrazino](oxo)-acetate reacted with nitrogen-containing nucleophiles (ammonia, hydrazine hydrate, aniline, and phenylhydrazine) to give linear of cyclic products.
- Subjects
NITROGUANIDINE; RING formation (Chemistry); CARBOXYLIC acids; ETHYLENE; SUCCINIC acid; NITROGEN compounds
- Publication
Russian Journal of Organic Chemistry, 2004, Vol 40, Issue 12, p1737
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1007/s11178-005-0091-4