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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
Article

Abstract

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.

Keywords

Aniline Hydrazine Triazole Succinic Acid Hydrazide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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