Russian Journal of Organic Chemistry

, Volume 40, Issue 12, pp 1737–1743 | Cite as

2-nitroguanidine derivatives: VIII. Synthesis and cyclizations of N1,N2-bis(N2- nitrocarbamimidoyl) dicarboxylic acid dihydrazides and ethyl [2-(N2-nitrocarbamimidoyl)-hydrazino](oxo)acetate

  • E. L. Metelkina
  • T. A. Novikova


New methods of synthesis of N1,N2-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 of N1, N2-bis(N2-nitrocarbamimidoyl) dihydrazides derived from malonic and succinic acids afforded the corresponding bis(3-nitroamino-1,2,4-triazol-5-yl)-alkanes, while N1,N2-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.


Aniline Hydrazine Triazole Succinic Acid Hydrazide 
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Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • E. L. Metelkina
    • 1
  • T. A. Novikova
    • 1
  1. 1.St. Petersburg State Institute of TechnologySt. PetersburgRussia

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