A facile synthesis of benzofuro[2,3-c]pyridines has been achieved under mild conditions by using ammonium acetate as the nitrogen source through intramolecular cascade annulation.This reaction could efficiently constr...A facile synthesis of benzofuro[2,3-c]pyridines has been achieved under mild conditions by using ammonium acetate as the nitrogen source through intramolecular cascade annulation.This reaction could efficiently construct pyridine ring and furan ring in one step.Moreover,the key annulation step was demonstrated through dihydrobenzofuran intermediates.展开更多
The crystal structure of the new title compound （E）-ethyl 6-benzyl-2-[（cyclopropylmethylamino）（4-fluorophenylamino）methyleneamino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate ethanol monosolvate （C28H...The crystal structure of the new title compound （E）-ethyl 6-benzyl-2-[（cyclopropylmethylamino）（4-fluorophenylamino）methyleneamino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate ethanol monosolvate （C28H31FN 4O2S·C2H6O, Mr=552.70） has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic system, space group P21/c with a=13.806（10）, b=10.850（7）, c=19.938（14）, β=98.842（9）° , V=2951（4）3 , Z=4, Dc=1.244g/cm 3 , F（000）=1176, μ=0.153 mm-1 , MoKα radiation （λ=0.71073）, R=0.0758 and wR=0.2234 for 4262 observed reflections with I 〉 2σ（I）. Intramolecular N-H…S and C-H…N interactions as well as intermolecular N-H…O and O-H…N hydrogen bonds help to stabilize the crystal structure. X-ray diffraction analysis reveals that the asymmetric unit contains one title molecule and one ethanol molecule.展开更多
The title compound 8-chloro-3-（（4-chlorobenzyl）thio）-[1,2,4]triazolo[4,3-a]pyridine was prepared from 1-chloro-4-（chloromethyl）benzene and 8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3（2H）-thione in the presence o...The title compound 8-chloro-3-（（4-chlorobenzyl）thio）-[1,2,4]triazolo[4,3-a]pyridine was prepared from 1-chloro-4-（chloromethyl）benzene and 8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3（2H）-thione in the presence of Na OH, and its structure was determined by X-ray diffraction analysis. The crystal is of triclinic system, space group P1 with a = 6.8264（6）, b = 7.5890（4）, c = 13.0960（7） A, α = 93.447（4）, β = 98.772（6）, γ = 92.615（6）o, V = 668.26（8） A3, Z = 2, the final R = 0.035 and wR = 0.09 for 2259 observed reflections with I 〉 2σ（I）. The preliminary biological test showed that the title compound has activities against Stemphylium lycopersici（Enjoji） Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory to be 51.19%, 62.02% and 15.56%, respectively.展开更多
To address the issues of reduced performance and shortened lifespan during the low-carbonizating process of Al_(2)O_(3)-C refractories,nano-crystalline ZrC modified graphite was prepared using Zr powder and flake grap...To address the issues of reduced performance and shortened lifespan during the low-carbonizating process of Al_(2)O_(3)-C refractories,nano-crystalline ZrC modified graphite was prepared using Zr powder and flake graphite as raw materials,with NaCl and NaF mixed salt serving as the medium.The flake graphite was gradually replaced by ZrC modified graphite in the preparation of Al_(2)O_(3)-C refractories,and its impact on the material’s structure and properties was investigated.The results indicate that,compared to samples with only flake graphite,the introduction of 1 mass%to 5 mass%nano-crystalline ZrC modified graphite can significantly enhance the mechanical performance of low-carbon Al_(2)O_(3)-C refractories.When 5 mass%ZrC modified graphite is added,the mechanical properties of the samples are optimal,with the cold modulus of rupture and elastic modulus reaching 22.5 MPa and 65.0 GPa,respectively.展开更多
A new dimeric Mn（Ⅱ） complex,namely,[Mn（L）（PIP）]_2·H_2O（1）,was synthesized under hydrothermal condition（H_2L = 3-carboxy-1-carboxymethyl-2-oxidopyridinium and PIP = 2-（pyridin-3-yl）-1H-imidazo[4,5-f][1...A new dimeric Mn（Ⅱ） complex,namely,[Mn（L）（PIP）]_2·H_2O（1）,was synthesized under hydrothermal condition（H_2L = 3-carboxy-1-carboxymethyl-2-oxidopyridinium and PIP = 2-（pyridin-3-yl）-1H-imidazo[4,5-f][1,10]phenanthroline）.It crystallizes in triclinic,space group P1 with a = 9.2037（13）,b = 9.6794（13）,c = 14.649（3） A,α = 94.858（3）,β = 94.928（3）,γ = 114.468（2）o,V = 1172.9（3） A^3,Z = 1,C_（52）H_（34）Mn_2N_（12）O_（11）,Mr = 1112.79,Dc = 1.575 g/cm^3,F（000） = 568,μ（Mo Ka） = 0.618 mm^-1,R = 0.0432 and w R = 0.1151.In 1,two L anions bridge two Mn（Ⅱ） atoms to give a dimeric [Mn（L）（PIP）] unit with the Mn···Mn distance of 3.009（2） A.The two PIP ligands are located on both sides of the dimer,which provides suitable π-π stacking interactions between PIP ligands.By these π-π stacking interactions,adjacent dimers are extended into a two-dimensional supramolecular layer.Further,the strong N–H···O hydrogen bond stabilizes the supramolecular layer structure of 1.Moreover,the thermal behavior and luminescent property of 1 have been studied.展开更多
Under regular heating and microwave irradiation, 3-alkyl substituted imidazo[1,5-a] pyridines were synthesized from 2,2＇- pyridil, di-2-pyridyl ketone and aliphatic aldehydes in the presence of ammonium acetate and a...Under regular heating and microwave irradiation, 3-alkyl substituted imidazo[1,5-a] pyridines were synthesized from 2,2＇- pyridil, di-2-pyridyl ketone and aliphatic aldehydes in the presence of ammonium acetate and acetic acid. Compared to the traditional heating condition, the reaction time under microwave irradiation was shorter and 3-alkyl imidazo[1,5-a]pyddines were given in higher yield.展开更多
Several new pyrazolo[4,3-b] pyridines 7a, b were prepared by reacting arylidenemalononitriles 1a, c or 1i, j with 4-nitrosoantipyrine 4. Reacting 1a, b, d with 4-azidomethylcarbonylantipyrine 8 give 2-aminopyrrole 14....Several new pyrazolo[4,3-b] pyridines 7a, b were prepared by reacting arylidenemalononitriles 1a, c or 1i, j with 4-nitrosoantipyrine 4. Reacting 1a, b, d with 4-azidomethylcarbonylantipyrine 8 give 2-aminopyrrole 14. Pyrano[3,2-c] quinolines 20a, b and 23 were obtained by reacting 4-hydroxyquinoline 15 with 1g, h, 2b respectively. Reaction of 1 with naphthalenediols 24, 27 and 29 yield naphthodipyrans 26a, b, 28a, b and 30a。展开更多
A series of diarylureas and diarylamides possessing pyrrolo[3,2-c]pyridine scaffold was designed and synthesized. Their in vitro antiproliferative activities were tested against a panel of 49 cell lines of eight diffe...A series of diarylureas and diarylamides possessing pyrrolo[3,2-c]pyridine scaffold was designed and synthesized. Their in vitro antiproliferative activities were tested against a panel of 49 cell lines of eight different cancer types at the NCI and compared with Sorafenib as a reference compound. Most of the compounds showed strong and broad-spectrum antiproliferative activities with superior potencies to Sorafenib. Compounds 8a, 9d and 9f showed lethal effect with mean %inhibition more than 100% over the 49 tested cell lines. In addition, the mean %inhibition results of compounds 8d, 8e, 9e, 9g and 9h were more than 80%. And most of the IC50 values of the target compounds were in submicromolar scale. Compounds 8a, 9b and 9e demonstrated high selectivity towards cancer cell lines compared with NIH3T3 fibroblasts.展开更多
2-Amino-4-benzoyl-1-arylpyrrole-3-carbonitriles react with arylidene malonodinitriles, β-ketoesters and β- diketones to afford pyrrolo[2,3-b]pyridine derivatives.
The title compound 6-chloro-l-（（6-chloropyridin-3-yl）methyl）-3-phenyl-lH-benzofuro[3,2-c]pyrazole（5,C21H13Cl2N3O,Mr = 394.26） was synthesized and characterized by elemental analysis,^1H NMR,^13C NMR and X-ray si...The title compound 6-chloro-l-（（6-chloropyridin-3-yl）methyl）-3-phenyl-lH-benzofuro[3,2-c]pyrazole（5,C21H13Cl2N3O,Mr = 394.26） was synthesized and characterized by elemental analysis,^1H NMR,^13C NMR and X-ray single-crystal diffraction.The structure reveals that the crystal belongs to the triclinic system,space group P1 with a = 7.8829（8）,b = 10.3281（10）,c = 11.7615（12）A°,α = 83.5552（2）,β = 79.921（2）,γ = 70.189（2）°,V= 885.54（15） A°3,Z = 2,Dc =1.479 g/cm^3,μ = 0.383 mm^-1,F（000） = 404,R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I 〉 2σ（I）.The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction.In addition,the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.展开更多
The synthesis of the bis-isoxazolyl-1,2,5,6-tetrahydro pyridine-3-carboxylates is achieved in high yield without the production of toxic waste products by using room temperature ionic liquid (RTILs) triethyl ammonium ...The synthesis of the bis-isoxazolyl-1,2,5,6-tetrahydro pyridine-3-carboxylates is achieved in high yield without the production of toxic waste products by using room temperature ionic liquid (RTILs) triethyl ammonium acetate (TEAA). The RTIL TEAA played the dual role of efficient green solvent as well as recyclable catalyst.展开更多
The investigation of complexation of uranium with biological active ligands is vital for understanding uranium speciation in biosystems. A number of studies have been undertaken for investigating the complexation of u...The investigation of complexation of uranium with biological active ligands is vital for understanding uranium speciation in biosystems. A number of studies have been undertaken for investigating the complexation of uranium in its (VI) oxidation states but similar investigations pertaining to the interaction of uranium, in lower oxidation states, with biological ligands is scarce. The aim of the work is to bridge this gap and studies have been carried out to determine the coordination pattern of pyridine-3-carboxylic acid with uranium(IV). Semi-micro analysis, spectro-analytical techniques, magnetic susceptibility and cyclic voltammetry have been employed for the characterization of the synthesized complex.展开更多
The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by densit...The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the PW91/DNP level. Vibration analysis was carried out to confirm the transition state structure. Reaction pathways were investigated in this study. The result indicates that the reaction Re→ TSB1→IMB1→ TSB2→ IMB2→TSB3→IMB3→TSB4→IMB4→TSB5→IMB5→TSB6→IMB6→TSB7→IMB7→ TSB8→IMB8→TSB9→IMB9→P2 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the experiment results.展开更多
基金This work was financially supported by the Natural Science Foundation of Henan Province(No.132300410319)and Luoyang Normal University.
文摘A facile synthesis of benzofuro[2,3-c]pyridines has been achieved under mild conditions by using ammonium acetate as the nitrogen source through intramolecular cascade annulation.This reaction could efficiently construct pyridine ring and furan ring in one step.Moreover,the key annulation step was demonstrated through dihydrobenzofuran intermediates.
基金Supported by the National Natural Science Foundation of China (No.21102084)the Key Project of Hubei Provincial Department of Education (No.D20091301)Doctoral Startup Foundation of China Three Gorges University (No.KJ2009B004)
文摘The crystal structure of the new title compound （E）-ethyl 6-benzyl-2-[（cyclopropylmethylamino）（4-fluorophenylamino）methyleneamino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate ethanol monosolvate （C28H31FN 4O2S·C2H6O, Mr=552.70） has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic system, space group P21/c with a=13.806（10）, b=10.850（7）, c=19.938（14）, β=98.842（9）° , V=2951（4）3 , Z=4, Dc=1.244g/cm 3 , F（000）=1176, μ=0.153 mm-1 , MoKα radiation （λ=0.71073）, R=0.0758 and wR=0.2234 for 4262 observed reflections with I 〉 2σ（I）. Intramolecular N-H…S and C-H…N interactions as well as intermolecular N-H…O and O-H…N hydrogen bonds help to stabilize the crystal structure. X-ray diffraction analysis reveals that the asymmetric unit contains one title molecule and one ethanol molecule.
基金funded by the National Natural Science Foundation of China(No.21002090)the Natural Science Foundation of Zhejiang Province(No.LY16C140007)the public program of Science and Technology of Zhejiang Province(2014C31127,2013C32SA700134)
文摘The title compound 8-chloro-3-（（4-chlorobenzyl）thio）-[1,2,4]triazolo[4,3-a]pyridine was prepared from 1-chloro-4-（chloromethyl）benzene and 8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3（2H）-thione in the presence of Na OH, and its structure was determined by X-ray diffraction analysis. The crystal is of triclinic system, space group P1 with a = 6.8264（6）, b = 7.5890（4）, c = 13.0960（7） A, α = 93.447（4）, β = 98.772（6）, γ = 92.615（6）o, V = 668.26（8） A3, Z = 2, the final R = 0.035 and wR = 0.09 for 2259 observed reflections with I 〉 2σ（I）. The preliminary biological test showed that the title compound has activities against Stemphylium lycopersici（Enjoji） Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory to be 51.19%, 62.02% and 15.56%, respectively.
文摘To address the issues of reduced performance and shortened lifespan during the low-carbonizating process of Al_(2)O_(3)-C refractories,nano-crystalline ZrC modified graphite was prepared using Zr powder and flake graphite as raw materials,with NaCl and NaF mixed salt serving as the medium.The flake graphite was gradually replaced by ZrC modified graphite in the preparation of Al_(2)O_(3)-C refractories,and its impact on the material’s structure and properties was investigated.The results indicate that,compared to samples with only flake graphite,the introduction of 1 mass%to 5 mass%nano-crystalline ZrC modified graphite can significantly enhance the mechanical performance of low-carbon Al_(2)O_(3)-C refractories.When 5 mass%ZrC modified graphite is added,the mechanical properties of the samples are optimal,with the cold modulus of rupture and elastic modulus reaching 22.5 MPa and 65.0 GPa,respectively.
基金Supported by the Institute Foundation of Siping city(No.2013036)
文摘A new dimeric Mn（Ⅱ） complex,namely,[Mn（L）（PIP）]_2·H_2O（1）,was synthesized under hydrothermal condition（H_2L = 3-carboxy-1-carboxymethyl-2-oxidopyridinium and PIP = 2-（pyridin-3-yl）-1H-imidazo[4,5-f][1,10]phenanthroline）.It crystallizes in triclinic,space group P1 with a = 9.2037（13）,b = 9.6794（13）,c = 14.649（3） A,α = 94.858（3）,β = 94.928（3）,γ = 114.468（2）o,V = 1172.9（3） A^3,Z = 1,C_（52）H_（34）Mn_2N_（12）O_（11）,Mr = 1112.79,Dc = 1.575 g/cm^3,F（000） = 568,μ（Mo Ka） = 0.618 mm^-1,R = 0.0432 and w R = 0.1151.In 1,two L anions bridge two Mn（Ⅱ） atoms to give a dimeric [Mn（L）（PIP）] unit with the Mn···Mn distance of 3.009（2） A.The two PIP ligands are located on both sides of the dimer,which provides suitable π-π stacking interactions between PIP ligands.By these π-π stacking interactions,adjacent dimers are extended into a two-dimensional supramolecular layer.Further,the strong N–H···O hydrogen bond stabilizes the supramolecular layer structure of 1.Moreover,the thermal behavior and luminescent property of 1 have been studied.
基金the Jiangsu Provincial Natural Science Foundation of China （No. BK2004092） the Scientific Research Foundation for the Returned 0verseas Chinese Scholars from State Education Ministry of China Nanjing University Talent Development Foundation.
文摘Under regular heating and microwave irradiation, 3-alkyl substituted imidazo[1,5-a] pyridines were synthesized from 2,2＇- pyridil, di-2-pyridyl ketone and aliphatic aldehydes in the presence of ammonium acetate and acetic acid. Compared to the traditional heating condition, the reaction time under microwave irradiation was shorter and 3-alkyl imidazo[1,5-a]pyddines were given in higher yield.
文摘Several new pyrazolo[4,3-b] pyridines 7a, b were prepared by reacting arylidenemalononitriles 1a, c or 1i, j with 4-nitrosoantipyrine 4. Reacting 1a, b, d with 4-azidomethylcarbonylantipyrine 8 give 2-aminopyrrole 14. Pyrano[3,2-c] quinolines 20a, b and 23 were obtained by reacting 4-hydroxyquinoline 15 with 1g, h, 2b respectively. Reaction of 1 with naphthalenediols 24, 27 and 29 yield naphthodipyrans 26a, b, 28a, b and 30a。
文摘A series of diarylureas and diarylamides possessing pyrrolo[3,2-c]pyridine scaffold was designed and synthesized. Their in vitro antiproliferative activities were tested against a panel of 49 cell lines of eight different cancer types at the NCI and compared with Sorafenib as a reference compound. Most of the compounds showed strong and broad-spectrum antiproliferative activities with superior potencies to Sorafenib. Compounds 8a, 9d and 9f showed lethal effect with mean %inhibition more than 100% over the 49 tested cell lines. In addition, the mean %inhibition results of compounds 8d, 8e, 9e, 9g and 9h were more than 80%. And most of the IC50 values of the target compounds were in submicromolar scale. Compounds 8a, 9b and 9e demonstrated high selectivity towards cancer cell lines compared with NIH3T3 fibroblasts.
文摘2-Amino-4-benzoyl-1-arylpyrrole-3-carbonitriles react with arylidene malonodinitriles, β-ketoesters and β- diketones to afford pyrrolo[2,3-b]pyridine derivatives.
基金supported by the National Natural Science Foundation of China(No.21002048)the Project of Outstanding Young Teachers in Guangdong Province(No.C1032190)
文摘The title compound 6-chloro-l-（（6-chloropyridin-3-yl）methyl）-3-phenyl-lH-benzofuro[3,2-c]pyrazole（5,C21H13Cl2N3O,Mr = 394.26） was synthesized and characterized by elemental analysis,^1H NMR,^13C NMR and X-ray single-crystal diffraction.The structure reveals that the crystal belongs to the triclinic system,space group P1 with a = 7.8829（8）,b = 10.3281（10）,c = 11.7615（12）A°,α = 83.5552（2）,β = 79.921（2）,γ = 70.189（2）°,V= 885.54（15） A°3,Z = 2,Dc =1.479 g/cm^3,μ = 0.383 mm^-1,F（000） = 404,R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I 〉 2σ（I）.The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction.In addition,the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.
文摘The synthesis of the bis-isoxazolyl-1,2,5,6-tetrahydro pyridine-3-carboxylates is achieved in high yield without the production of toxic waste products by using room temperature ionic liquid (RTILs) triethyl ammonium acetate (TEAA). The RTIL TEAA played the dual role of efficient green solvent as well as recyclable catalyst.
文摘The investigation of complexation of uranium with biological active ligands is vital for understanding uranium speciation in biosystems. A number of studies have been undertaken for investigating the complexation of uranium in its (VI) oxidation states but similar investigations pertaining to the interaction of uranium, in lower oxidation states, with biological ligands is scarce. The aim of the work is to bridge this gap and studies have been carried out to determine the coordination pattern of pyridine-3-carboxylic acid with uranium(IV). Semi-micro analysis, spectro-analytical techniques, magnetic susceptibility and cyclic voltammetry have been employed for the characterization of the synthesized complex.
基金Project supported by the Scientific and Technological Research Program of Chongqing Municipal Education Commission(KJ1601215,KJ15012002)the Ministry of Education “Chunhui Plan”(Z2016177)
文摘The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the PW91/DNP level. Vibration analysis was carried out to confirm the transition state structure. Reaction pathways were investigated in this study. The result indicates that the reaction Re→ TSB1→IMB1→ TSB2→ IMB2→TSB3→IMB3→TSB4→IMB4→TSB5→IMB5→TSB6→IMB6→TSB7→IMB7→ TSB8→IMB8→TSB9→IMB9→P2 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the experiment results.
