- Synthesis of N-alkylated derivatives of imidazole as antibacterial agents
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N-Alkylation of imidazole, 2-methylimidazole and 2-methyl-4-nitroimidazole have been carried out to achieve effective antibacterial agents. The products were then investigated for antibacterial activity against Escherichia coil, Staphylococcus aureus and Pseudomonas aeruginosa. Antibacterial effects of 1-alkylimidazole derivatives increase as the number of carbons in alkyl chain increases up to nine carbons. Also substitution of 2-methyl and 2-methyl-4-nitro groups on imidazole ring increases the antibacterial activity.
- Khabnadideh,Rezaei,Khalafi-Nezhad,Bahrinajafi,Mohamadi,Farrokhroz
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- Transition-metal-catalyzed arylation of nitroimidazoles and further transformations of manipulable nitro group
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Pd- or Ni-catalyzed C-H arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on regioselectivity of the reaction. In addition, we have shown that the efficiency of the Suzuki-Miyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct C-H arylation. The exploration of the chemical potential of the nitro group and a putative reaction mechanism are discussed.
- Iaroshenko, Viktor O.,Gevorgyan, Ashot,Mkrtchyan, Satenik,Arakelyan, Knar,Grigoryan, Tatevik,Yedoyan, Julietta,Villinger, Alexander,Langer, Peter
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p. 2103 - 2119
(2015/04/14)
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- Synthesis, limitations, and thermal properties of energetically- substituted, protonated imidazolium picrate and nitrate salts and further comparison with their methylated analogs
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The possibility of forming simple energetic ionic liquids via the straightforward protonation of heterocyclic amines with nitric or picric acid was explored with 1-alkylimidazoles, 1-alkyl-2-methylimidazoles, and nitro, dinitro, and dicyano-substituted derivatives. The melting points of most of the prepared salts were lower than expected and of the 30 compounds prepared, more than half were found to melt below 100 °C. Limitations in the approach were found as a result of the use of energetic electron withdrawing substituents, such as nitro or cyano, which results in a reduction in nucleophilicity of the heterocycle and an inability to form salts with the acids studied. Interesting thermal behavior was observed with several of the new salts including supercooling and crystallization on heating. Comparison of the simple protonated imidazolium nitrate and picrate salts with their methylated analogs indicated that the protonated ionic liquids do not differ substantially in their melting points from the methylated analogs. However, the thermal stabilities of protonated imidazolium salts are much lower than their alkylated derivatives. Nitrate salts with alkylated cations tend to be more thermally stable than the corresponding picrate salts, but with protonated cations, the picrate salts tend to be approximately 70-80 °C more stable than the nitrate salts. Moreover, accelerating rate calorimetry (ARC) revealed that alkylated salts decompose much less exothermically (in some cases endothermically) than the protonated analogs, and that among all the analyzed salts, the most energetic materials found were protonated 1-methylimidazolium nitrate and 1,2-dimethylimidazolium picrate. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.
- Smiglak, Marcin,Hines, C. Corey,Reichert, W. Matthew,Vincek, Adam S.,Katritzky, Alan R.,Thrasher, Joseph S.,Sun, Luyi,McCrary, Parker D.,Beasley, Preston A.,Kelley, Steven P.,Rogers, Robin D.
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experimental part
p. 702 - 722
(2012/05/04)
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- Solid-liquid phase-transfer catalytic method for N-alkylation of nitroimidazole
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A variety of 1-alkyl-2-methyl-4-nitroimidazoles have been synthesized with a solid-liquid phase-transfer catalytic method in excellent yields.
- Liu,Chen,Cao,Li
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p. 2611 - 2615
(2007/10/02)
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- A facile high yielding method for synthesis of N-alkyl-4-nitroimidazoles
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A high yielding and fast reaction for the synthesis of a variety of N-alkyl 4-nitroimidazoles has been described. This method involves reaction of 2-methyl-4(5)-nitro-1H-imidazole with suitable alkyl halides in K2CO3/DMF at 110-120°C.
- Bhujanga Rao,Gundu Rao,Sing
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p. 427 - 433
(2007/10/02)
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