Energetic Materials Based on N-substituted 4(5)-nitro-1,2,3-triazoles.

Gennady T Sukhanov,Vyacheslav I Krasnov,Yulia V Filippova,Yuri V Gatilov,Konstantin K Bosov,Ekaterina V Pivovarova,Anna G Sukhanova,Irina A Krupnova

doi:10.3390/ma15031119

Abstract

The regularities and synthetic potentialities of the alkylation of 4(5)-nitro-1,2,3-triazole in basic media were explored, and new energetic ionic and nitrotriazole-based coordination compounds were synthesized in this study. The reaction had a general nature and ended with the formation of N1-, N2-, and N3-alkylation products, regardless of the conditions and reagent nature (alkyl- or aryl halides, alkyl nitrates, dialkyl sulfates). This reaction offers broad opportunities for expanding the variability of substituents on the nitrotriazole ring in the series of primary and secondary aliphatic, alicyclic, and aromatic substituents, which is undoubtedly crucial for solving the problems related to both high-energy materials development and medicinal chemistry when searching for new efficient bioactive compounds. An efficient methodology for the separation of regioisomeric N-alkyl(aryl)nitrotriazoles has been devised and relies on the difference in their basicity and reactivity during quaternization and complexation reactions. Based on the inaccessible N3-substitution products that exhibit a combination of properties of practical importance, a series of energy-rich ionic systems and coordination compounds were synthesized that are gaining ever-increasing interest for the chemistry of energy-efficient materials, coordination chemistry, and chemistry of ionic liquids.

Highlights

IntroductionThe reaction had a general nature and ended with the formation of N1-, N2-, and N3-alkylation products, regardless of the conditions and reagent nature (alkyl- or aryl halides, alkyl nitrates, dialkyl sulfates)
Laboratory for Chemistry and Technology of High-Energy Azoles, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Department of Chemistry, Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian
1,2,3-Triazole derivatives are viewed as the valuable building block for the molecular construction of a wide array of new compounds with various properties of practical importance

Summary

Introduction

The reaction had a general nature and ended with the formation of N1-, N2-, and N3-alkylation products, regardless of the conditions and reagent nature (alkyl- or aryl halides, alkyl nitrates, dialkyl sulfates). This reaction offers broad opportunities for expanding the variability of substituents on the nitrotriazole ring in the series of primary and secondary aliphatic, alicyclic, and aromatic substituents, which is undoubtedly crucial for solving the problems related to both high-energy materials development and medicinal chemistry when searching for new efficient bioactive compounds. A number of drugs that contain 1,2,3-triazole moieties, including TSAO [4] (anti-HIV agent), Cefatrizine [5] (antibiotic), CAI [6] (anticancer agent), and Tazobactum [7] (antibacterial agent) are currently used in clinical applications (Figure 1)

Methods

Results

Conclusion