One new benzimidazole derivative copper（II） complex 1（C10H6Cu N2, Mr = 217.71） has been synthesized and characterized by FT-IR and X-ray single-crystal diffraction. It crystallizes in orthorhombic, space group Pbc...One new benzimidazole derivative copper（II） complex 1（C10H6Cu N2, Mr = 217.71） has been synthesized and characterized by FT-IR and X-ray single-crystal diffraction. It crystallizes in orthorhombic, space group Pbcn with a = 17.417（2）, b = 8.9963（8）, c = 11.3432（9） ？, V = 1777.3（3） ？3, Z = 8, μ（Mo Kα） = 2.403, F（000） = 872, Dc = 1.627 g/cm3. The final R = 0.0598 for 1153 observed reflections with I 〉 2σ（I） and w R = 0.17 for all data. The in vitro anti-cancer activities of 1, Cu Cl2 and the benzimidazole ligand L were investigated using human cervical（Hela） and hepatocellular carcinoma（Hep-G2） cancer cell lines. The copper（II） complex can greatly inhibit the cell proliferation and show stronger cytotoxic activities against the tested cancer cell lines than both the ligand and copper（II） salt.展开更多
cis-1,2-Disubstituted cyclododecanes 2 were synthesized by sodium borohydride reduction of 2-monosubstituted cyclododecanones and their structures were confirmed by 1HNMR, ^13C NMR and elemental analysis. The higher c...cis-1,2-Disubstituted cyclododecanes 2 were synthesized by sodium borohydride reduction of 2-monosubstituted cyclododecanones and their structures were confirmed by 1HNMR, ^13C NMR and elemental analysis. The higher cis-selectivity of NaBH4 reduction of 2- monosubstituted cyclododecanones was rationalized by the mode of ＂corner position carbonyl participation＂. Crystal data for 2c： Mr = 263.21, monoclinic, space group P21/c, a = 1.11140（7）, b = 2.62590（17）, c = 0.91360（6） nm, β= 106.1840（10）°, V = 2.5606（3） nm^3, Dc = 1.366 g/cm^3, Z = 8, F（000） = 1104, μ（MoKα= 3.182 mm^-1, S = 0.837, the final R = 0.0460 and wR = 0.1033. Crystal X-ray diffraction analysis for 2c showed that its ring skeleton adopts [3333] conformation, in which the OH group presents at the side-exo position and the other one at the corner carbon. The 1H NMR data of 2 showed that 1-corner-R-2-side-exo-OH [3333] and 1-corner-OH-2-side-exo-R [3333] conformations coexist in dynamic equilibrium in the solution, but only the former presents in the crystal.展开更多
A novel and efficient approach to the synthesis of 2-substituted benzimidazoles has been developed via CuI/DMEDA-catalyzed coupling reaction and post-cyclization with glacial acetic acid from readily available 2-iodoa...A novel and efficient approach to the synthesis of 2-substituted benzimidazoles has been developed via CuI/DMEDA-catalyzed coupling reaction and post-cyclization with glacial acetic acid from readily available 2-iodoanilines and amides. This method is suitable for the construction of a variety of benzimidazoles in moderate to good yields under short reaction times.展开更多
1,2-Disubstituted benzimidazoles are selectively synthesized in high yields under extremely mild conditions via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of i...1,2-Disubstituted benzimidazoles are selectively synthesized in high yields under extremely mild conditions via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of iron（Ⅲ） phosphate under solventfree conditions. The use of readily available iron（Ⅲ） phosphate as a reusable and recyelable catalyst makes this process quite simple, convenient, and environment-friendly.展开更多
Some new 4H-pyrrolo[1,2-a]benzimidazoles（2a-2f） have been synthesized. The structures of these compounds were confirmed by IR, tH NMR, mass spectroscopy and elemental analysis. Compound 2a was further confirmed by X...Some new 4H-pyrrolo[1,2-a]benzimidazoles（2a-2f） have been synthesized. The structures of these compounds were confirmed by IR, tH NMR, mass spectroscopy and elemental analysis. Compound 2a was further confirmed by X-ray diffraction. The in vitro antimicrobial activities of these compounds were determined against some gram-positive bacteria, gram-negative bacteria and fungi and their drug-resistant isolates in comparison with standard drugs. Antimicrobial results indicate that compounds 2c, 2d and 2e show moderately active antibacterial properties, their minimum inhibitory concentrations are from 12.5 μg/mL to 125 μg/mL. In the series, the most active compound against C. albicans is compound 2fwith an MIC value of 31.25 μg/mL.展开更多
The syntheses of a variety of 1,3,5-triazinebenzimidazoles obtained by the cyclocondensafion reaction of 2-guanidinobenzimidazole with a series of meta-substituted benzaldehydes were reported. The prepared compounds w...The syntheses of a variety of 1,3,5-triazinebenzimidazoles obtained by the cyclocondensafion reaction of 2-guanidinobenzimidazole with a series of meta-substituted benzaldehydes were reported. The prepared compounds were fully characterized by IR and NMR spectroscopies. Based on the density functional theory（DFT） calculations method, quantum chemical calculations were performed by Gaussian 09 set of programs. All possible transition states, reactants and products were fully optimized at the hybrid density functional B3LYP level using the 6-311＋G（d,p）. The geometries of five possible tautomers of 2-amino-4-aryl[1,3,5]triazino[1,2-a]benzimidazoles were optimized in ethanol, using conductor like polarizable confinuum（CPCM） in the gas phase. The energetic diagrams of tautomeric equilibrium showed that form A is the most stable tautomer which proved to be in accordance with the X-ray diffraction structure analysis. In order to interpret the reaction mechanism, the chemical reactivity was studied using local and global reactivity indexes.展开更多
One-pot condensation of 2-aminothiophenol or 1,2-phenylenediamine with different aldehydes has been catalyzed by hexamethylenetetramine-bromine（HMTA-Bromine） as new,available and effective catalyst.2-Arylbenzo thiaz...One-pot condensation of 2-aminothiophenol or 1,2-phenylenediamine with different aldehydes has been catalyzed by hexamethylenetetramine-bromine（HMTA-Bromine） as new,available and effective catalyst.2-Arylbenzo thiazoles and 2-aryl benzimidazoles have been achieved in excellent yield and good purity.展开更多
基金financially supported by the Natural Science Foundation of Guangxi Province(No.2010GXNSF)Youth Science Foundation of Guangxi Medical University(No.02604001015)
文摘One new benzimidazole derivative copper（II） complex 1（C10H6Cu N2, Mr = 217.71） has been synthesized and characterized by FT-IR and X-ray single-crystal diffraction. It crystallizes in orthorhombic, space group Pbcn with a = 17.417（2）, b = 8.9963（8）, c = 11.3432（9） ？, V = 1777.3（3） ？3, Z = 8, μ（Mo Kα） = 2.403, F（000） = 872, Dc = 1.627 g/cm3. The final R = 0.0598 for 1153 observed reflections with I 〉 2σ（I） and w R = 0.17 for all data. The in vitro anti-cancer activities of 1, Cu Cl2 and the benzimidazole ligand L were investigated using human cervical（Hela） and hepatocellular carcinoma（Hep-G2） cancer cell lines. The copper（II） complex can greatly inhibit the cell proliferation and show stronger cytotoxic activities against the tested cancer cell lines than both the ligand and copper（II） salt.
基金Presented in part at the Third National Symposium of the Chinese Chemical Society on Organic Chemistry, Lanzhou, China, August, 2004 (for abstract, see Chin. J. Org. Chem., 2004, Suppl. 365)This project was supported by the National Natural Science Foundation of China (No. 20072053)
文摘cis-1,2-Disubstituted cyclododecanes 2 were synthesized by sodium borohydride reduction of 2-monosubstituted cyclododecanones and their structures were confirmed by 1HNMR, ^13C NMR and elemental analysis. The higher cis-selectivity of NaBH4 reduction of 2- monosubstituted cyclododecanones was rationalized by the mode of ＂corner position carbonyl participation＂. Crystal data for 2c： Mr = 263.21, monoclinic, space group P21/c, a = 1.11140（7）, b = 2.62590（17）, c = 0.91360（6） nm, β= 106.1840（10）°, V = 2.5606（3） nm^3, Dc = 1.366 g/cm^3, Z = 8, F（000） = 1104, μ（MoKα= 3.182 mm^-1, S = 0.837, the final R = 0.0460 and wR = 0.1033. Crystal X-ray diffraction analysis for 2c showed that its ring skeleton adopts [3333] conformation, in which the OH group presents at the side-exo position and the other one at the corner carbon. The 1H NMR data of 2 showed that 1-corner-R-2-side-exo-OH [3333] and 1-corner-OH-2-side-exo-R [3333] conformations coexist in dynamic equilibrium in the solution, but only the former presents in the crystal.
基金Acknowledgement We are grateful for support of this project by the National Natural Science Foundation of China （No. J1103307） and the project of Science Foundation of Gansu Province （No. 1208RJZA266）.
文摘A novel and efficient approach to the synthesis of 2-substituted benzimidazoles has been developed via CuI/DMEDA-catalyzed coupling reaction and post-cyclization with glacial acetic acid from readily available 2-iodoanilines and amides. This method is suitable for the construction of a variety of benzimidazoles in moderate to good yields under short reaction times.
文摘1,2-Disubstituted benzimidazoles are selectively synthesized in high yields under extremely mild conditions via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of iron（Ⅲ） phosphate under solventfree conditions. The use of readily available iron（Ⅲ） phosphate as a reusable and recyelable catalyst makes this process quite simple, convenient, and environment-friendly.
基金Supported by the Natural Science Foundation of Jiangsu Education Committee, China（No. 12KJD15008） and the National Natural Science Foundation of China（No.21202101）.
文摘Some new 4H-pyrrolo[1,2-a]benzimidazoles（2a-2f） have been synthesized. The structures of these compounds were confirmed by IR, tH NMR, mass spectroscopy and elemental analysis. Compound 2a was further confirmed by X-ray diffraction. The in vitro antimicrobial activities of these compounds were determined against some gram-positive bacteria, gram-negative bacteria and fungi and their drug-resistant isolates in comparison with standard drugs. Antimicrobial results indicate that compounds 2c, 2d and 2e show moderately active antibacterial properties, their minimum inhibitory concentrations are from 12.5 μg/mL to 125 μg/mL. In the series, the most active compound against C. albicans is compound 2fwith an MIC value of 31.25 μg/mL.
文摘The syntheses of a variety of 1,3,5-triazinebenzimidazoles obtained by the cyclocondensafion reaction of 2-guanidinobenzimidazole with a series of meta-substituted benzaldehydes were reported. The prepared compounds were fully characterized by IR and NMR spectroscopies. Based on the density functional theory（DFT） calculations method, quantum chemical calculations were performed by Gaussian 09 set of programs. All possible transition states, reactants and products were fully optimized at the hybrid density functional B3LYP level using the 6-311＋G（d,p）. The geometries of five possible tautomers of 2-amino-4-aryl[1,3,5]triazino[1,2-a]benzimidazoles were optimized in ethanol, using conductor like polarizable confinuum（CPCM） in the gas phase. The energetic diagrams of tautomeric equilibrium showed that form A is the most stable tautomer which proved to be in accordance with the X-ray diffraction structure analysis. In order to interpret the reaction mechanism, the chemical reactivity was studied using local and global reactivity indexes.
文摘One-pot condensation of 2-aminothiophenol or 1,2-phenylenediamine with different aldehydes has been catalyzed by hexamethylenetetramine-bromine（HMTA-Bromine） as new,available and effective catalyst.2-Arylbenzo thiazoles and 2-aryl benzimidazoles have been achieved in excellent yield and good purity.
