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1

Synthesis and Characterization of 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)ethan-1-one

Ji H., Niu Y., Liu D., Wang W., Dai C.

Polish Journal of Chemical Technology

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2017

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Vol. 19, nr 1

41--47

EN

A simple and efficient method to prepare 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)ethan-1-one via nucleophilic substitution of 2-chloro-1-(1-chlorocyclopropyl)ethanone and 1,2,4-triazole is described. The title compound is the key intermediate required for the synthesis of prothioconazole, a promising agricultural fungicide. By exploring changes in the reaction time, temperature, ratio of starting reagents, acid binding agent, and the nature of phase transfer catalyst, the reaction conditions could be optimized to afford the desired N-alkylated material in near-quantitative yield. The ultimate yield of the product after recrystallization was 93%, with a purity of 99% based on its characterization by Gas Chromatography-Mass Spectrometer (GC-MS), Fourier Transform infrared spectroscopy (IR), Proton Magnetic Resonance (1H NMR), and Carbon-13 Nuclear Magnetic Resonance (13C NMR). The synthetic process is suitable for industrial application, with the advantages of high yield and facile preparation under mild operating conditions.

2

Synthesis and biological activity of 1,2,4-triazolo-[3,4-b]thiadiazole as antimicrobial agents

Vekariya P. B., Pandya J. R., Goswami V., Joshi H. S.

International Letters of Chemistry, Physics and Astronomy

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2014

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Vol. 7

45--52

EN

Some novel 6-fluoro chroman derivatives having 1,2,4-triazolo-[3,4-b]thiadiazole were synthesized and characterized by IR, NMR and mass spectral analysis. All synthesized compounds were screened for antimicrobial activity using broth dilution method. All the compounds showed good antimicrobial activity and compound 5e showed significant antibacterial activity.

3

An efficient solid phase one port synthesis of Novel triazolo[1,5-a]pyrimidine derivatives from 4-(4-aminophenyl)morpholin-3-one and evaluation of their antimicrobial activity

Prajapati D. R., Vilapara K. V., Naliapara Y. T.

International Letters of Chemistry, Physics and Astronomy

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2014

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Vol. 14, iss. 1

12--21

EN

A series of novel triazolo[1,5-a]pyrimidine derivatives was synthesized from 5-amino-1,2,4-triazole and biologically active morpholinone amine in excellent yield as promising class of antimicrobial agents. The antimicrobial activities were investigated against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Staphylococcus pyogen, Candida albicans, Aspergillusniger, Aspergillusclavatus and compared with standard drugs Ampicillin, Chloramphenicol, Norfloxacin and Griseofulvin. All the synthesized compounds were characterized by IR, 1H NMR, 13C and mass spectroscopy. The result of antimicrobial activity data revealed that compound 4f,4g and 4i were found more active against bacterial species and compound 4c, 4d, 4g, 4i and 4jwere found more active against fungal strain, while other compounds shows moderate to law activity against microbes.

4

Thermal and Structural Properties of the Hg(II) Complexes with Some Amino and Mercapto Derivatives of 1,2,4-Triazole

Gabryszewski M., Wieczorek B.

Polish Journal of Chemistry

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2006

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Vol. 80, nr 5

709-717

EN

The complexes of Hg(II) with 3-amino-1,2,4-triazole, 4-amino-1,2,4-triazole, 3,5-diamino- 1,2,4-triazole, 3-amino-5-methylthio-1,2,4-triazole, 1H-1,2,4-triazole-3-thiol and 3-amino-5-mercapto-1,2,4-triazole have been prepared and characterized by elemental analysis, infrared spectra and thermal analysis. The ligands form 1:2 mononuclear and 1:1 polymeric complexes. The structure and the thermal decomposition of the complexes depend on the nature of donor atoms.

5

Computer Simulation of Thermal Decomposition Mechanism for Compounds with Nitroguanidine Fragment

Bakhmatova E. A., Korolev V. L., Pivina T. S., Porollo A. A.

Central European Journal of Energetic Materials

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2006

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Vol. 3, nr 4

3-12

EN

The application efficiency of energetic compounds depends on the set of their characteristics. The most important of them is a thermal stability, which is connected with the thermal decomposition mechanism of compounds. Nitroguanidine and its analogs have been of interest as an example of energetic compounds. However, currently there is no general view for the thermolysis of nitroguanidine analogs. Having labile hydrogen atoms, theoretically, nitroguanidine and its analogs may exist in different tautomeric forms. Meanwhile, there are no experimental evidences if this or other tautomeric form domination during a decomposition process. In order to fill this gap, the simulation of mechanism of all nitroguanidine tautomers and 3-nitramine-1,2,4-triazole thermal decomposition was carried out. Subsequent evaluation of different tautomeric forms in terms of thermodynamic stability and activation energy for initial steps of their decomposition reactions has been conducted using DFT approach (B3LYP/6-31G*). Thermochemical preferences of some decomposition pathways have been determined.

6

O zjawisku spin-crossover. Polimeryczne kompleksy Fe(II) z pochodnymi 1,2,4-triazolu

Połomka P.

Wiadomości Chemiczne

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2004

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[Z] 58, 5-6

477--496

EN

This paper is a short review of a spin-crossover phenomenon in complexes of iron(II). This phenomenon is related to the thermally induced transition between a diamagnetic low spin ground state (LS or S=0) and the excited paramagnetic high spin state (HS or S=2). Numerous compounds switch from a stable electronic state to another state in a reversible and detectable fashion in response to an appropriate and controllable external perturbation. This transition is accompanied by a strong thermochromism between rose and white colors. In certain cases, a hysteresis effect is accompanying this transition, which confers a memory effect to the system. The potential applications of spin transition (ST) molecular materials in the field of display and data processing has led to intensive studies of this phenomenon in the last ten years. For this purpose the compounds need to show a large thermal hysteresis, with the middle of the hysteresis loop falling as close as possible to room temperature. To achieve this goal iron(II) ST molecular materials are designed and synthesized as polymers in order to increase intermolecular interactions. In this paper some polymers based on 1,2,4-triazole derivatives are described because of their bridging nature leading to a strong cooperativity. The influence of various parameters, namely type of counter ion, R substituent in 4- position in the triazole ring, number of noncoordinated lattice water molecules, on the structure and ST regime of Fe(II)-1,2,4-triazole polymers is depicted. Some of the compounds presented might be of potential use as the electronic displays or switches.

7

Synthesis and characterization of the copper(II) complexes with 3-amino-1,2,4-triazole, 4-amino-1,2,4-triazole and 3-amino-5-methylthio-1,2,4-triazole

Gabryszewski M.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 12

2519-2523

EN

The complexes of Cu(II) with 3-amino-1,2,4-triazole, 4-amino-1,2,4-triazole and 3-amino-5-methylthio-1,2,4-triazole have been preparated and characterized by metal and CHN analyses, infrared and visible spectral and magnetic susceptibility data. It has been found, that the first two ligands from mononuclear species, while the third ligand forms the polynuclear complex. All the complexes have pseudo-octahedral configuration with a tetragonal distortion.