Organosulfur materials are a sustainable alternative to the present-day layered oxide cathodes in lithium-based batteries.One such organosulfur material that was intensely explored from the 1990s to early 2010s is 2,5...Organosulfur materials are a sustainable alternative to the present-day layered oxide cathodes in lithium-based batteries.One such organosulfur material that was intensely explored from the 1990s to early 2010s is 2,5-dimercapto-1,3,4-thiadiazole(DMCT).However,research interest declined as the electrode reactions with DMCT were assumed to be too sluggish to be practical.Armed with the advances in metal-sulfur batteries,we revisit DMCT-based materials in the form of poly[tetrathio-2,5-(1,3,4-thiadiazole)],referred to as pDMCT-S.With an appropriate choice of electrode design and electrolyte,pDMCT-S cathode paired with a Li-metal anode shows a capacity of 715 mA h g^(-1)and a Coulombic efficiency of 97.7%at a C/10 rate,thus quelling the concerns of sluggish reactions.Surprisingly,pDMCT-S shows significantly improved long-term cyclability compared to a sulfur cathode.Investigations into the origin of the stability reveals that the discharge product Li-DMCT in its mesomeric form can strongly bind to polysulfides,preventing their dissolution into the electrolyte and shuttling.This unique mechanism solves a critical problem faced by sulfur cathodes.Encouragingly,this mechanism results in a stable performance of pDMCT-S with Na-metal cells as well.This study opens the potential for exploring other organic materials that have inherent polysulfide sequestering capabilities,enabling long-life metal-sulfur batteries.展开更多
5-(4-Cyclopropyl-5-((3-fluorobenzyl)sulfonyl)-4H-1,2,4-triazol-3-yl)-4-methyl-1,2,3-thiadiazole was synthesized and recrystallized from Et OH. The compound was characterized by ^1H NMR,MS,elemental analysis and ...5-(4-Cyclopropyl-5-((3-fluorobenzyl)sulfonyl)-4H-1,2,4-triazol-3-yl)-4-methyl-1,2,3-thiadiazole was synthesized and recrystallized from Et OH. The compound was characterized by ^1H NMR,MS,elemental analysis and X-ray diffraction. The structure-active relationship and the antifungal activity based on density functional theory calculation(DFT) and antifungal activities were investigated. The compound crystallizes in the monoclinic space group P121/n1 with a = 8.929(3),b=12.715(4),c=15.161(5) A°,β = 106.142(3)o,V = 1653.3(9) A°3,Z = 4 and R = 0.0393 for 3930 observed reflections with I 〉 2σ(I). Theoretical calculation of the title compound was carried out with B3LYP/6-31G(d,p). The full geometry optimization was carried out using the 6-31G(d,p) basis set.The frontier orbital energy and atomic net charges were discussed. The observed results of the compound have been compared with theoretical results and the experimental data show good agreement with the calculated values. The compound exhibits good antifungal activity.展开更多
The title compound, [HgI2(C12H8N4S)], has been synthesized and characterized by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 14.086(2), b = 6.0365(6), c = ...The title compound, [HgI2(C12H8N4S)], has been synthesized and characterized by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 14.086(2), b = 6.0365(6), c = 20.286(2)°A,β= 108.818(5)°, V = 1632.7(3)°A^3, Mr = 694.67, Z = 4, D, = 2.826 g/cm^3,μ= 13.331 mm^-1, F(000) = 1240, S = 1.108, the final R = 0.0438 and wR = 0.0934 for 3085 observed reflections (I〉 2σ(I)). The Hg(Ⅱ) atom is coordinated by two 2,5-bis(4-pyridyl)-1,3,4-thiadiazole (L) molecules and two iodine anions in a distorted tetrahedral coordination geometry. Mercury atoms are linked by the organic ligands to form a one-dimensional zigzag chain. It is noteworthy that such 1D zigzag chains are extended into a two-dimensional double layer framework through I…I interactions展开更多
The title compound N-tert-butyl-N-(4-methyl-1,2,3-thiadiazole)-5-yl-N'-(4-me-thyl-1,2,3-thiadiazole)-5-formyl-N'-3,5-dichloropyrid-2-yl-diacylhydrazines (C18H17Cl2N7O3S2, Mr = 514.41) has been synthesized by t...The title compound N-tert-butyl-N-(4-methyl-1,2,3-thiadiazole)-5-yl-N'-(4-me-thyl-1,2,3-thiadiazole)-5-formyl-N'-3,5-dichloropyrid-2-yl-diacylhydrazines (C18H17Cl2N7O3S2, Mr = 514.41) has been synthesized by the reaction of N-tert-butyl-N'-3,6-dichloropyridine-2-formyl hydrazine with 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride and triethylamine, and its structure was characterized by 1H NMR, HR MS, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group C2/c with a = 27.726(8), b = 11.045(3), c = 14.507(4)A, β = 96.758(4)°, Z = 8, V = 4412(2) A^3, Dc = 1.549 g/cm^3, μ = 0.521 mm^-1, F(000) = 2112, R = 0.0405 and wR = 0.1153. X-ray analysis indicates that all rings are non-planar in this molecule. The bioassay results indicate that both the title compound and the positive control RH-5992 have weak fungicide activities, while the title compound has good insecticidal activity against Plutella xylostella L. and no insecticidal activity against Culex pipiens pallens.展开更多
The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate (C 14 H 10 N 2 O 2 S,M r=270.31) was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its ...The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate (C 14 H 10 N 2 O 2 S,M r=270.31) was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its structure was characterized by IR,1 H NMR,high-resolution mass spectrometry and single-crystal X-ray diffraction.The crystal belongs to orthorhombic,space group Pbcn with a=23.475(5),b=9.6640(19),c=10.814(2),β=90.00°,Z=8,V=2453.2(9) 3,M r=270.30,D c=1.464 g/cm 3,μ=0.262 mm-1,F(000)=1120,R=0.0444 and wR=0.1099.X-ray analysis revealed that the thiadiazole and naphthalene rings were non-planar,while the thiadiazole ring and the ester group were essentially planar,and two intermolecular hydrogen bonds C(6) H(6)···O(1) and C(14) H(14)···O(1) were observed.The preliminary biological test showed that the title compound had antifungal and antivirus activities against tobacco mosaic virus.展开更多
A facile one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles was achieved by ultrasonic irradiation of a mixture of 1-naphthylacetyl chloride, NH4CNS, CH2Cl2 and PEG-400 for 1.5 h at 10–20 °C and subsequen...A facile one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles was achieved by ultrasonic irradiation of a mixture of 1-naphthylacetyl chloride, NH4CNS, CH2Cl2 and PEG-400 for 1.5 h at 10–20 °C and subsequent irradiation for 1.5 h in the presence of N-arylglycine hydrazides. This method requires short time and gives thiadiazoles in high yields.展开更多
The title compound N-(tert-butyl)-N'-(2-(4-chlorophenyl)acetyl)-5-methyl-1,2,3-thiadiazole-4-carbohydrazide (C16H19ClN4NaO2S, Mr = 366.86) has been synthesized, and its structure was characterized by IR, 1H N...The title compound N-(tert-butyl)-N'-(2-(4-chlorophenyl)acetyl)-5-methyl-1,2,3-thiadiazole-4-carbohydrazide (C16H19ClN4NaO2S, Mr = 366.86) has been synthesized, and its structure was characterized by IR, 1H NMR, H RMS and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group Pī with a = 8.464(2), b = 10.192(2), c = 11.757(2), α = 68.48(3), β = 76.31(3), γ = 80.86(3)°, Z = 2, V = 2024.6(10) 3, Dc = 1.333 g/cm3, μ = 0.339 mm-1, F(000) = 384, R = 0.0450 and wR (Ⅰ 〉 2σ(Ⅰ)) = 0.1234. X-ray analysis indicates one N-H…N intermolecular hydrogen bond and no π-π stacking interactions are observed in this crystal structure. The preliminary biological test shows that the title compound has fungicidal activity and antivirus activities against tobacco mosaic virus.展开更多
The title compound N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N'-3,5-dichloro-4- (1,1,2,2- tetrafluoroethoxyl)phenyl urea (C13H8Cl2F4N4O3S, Mr = 447.19) has been synthesized from 4-methyl- 1,2,3-thiadiazole-5-carbon...The title compound N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N'-3,5-dichloro-4- (1,1,2,2- tetrafluoroethoxyl)phenyl urea (C13H8Cl2F4N4O3S, Mr = 447.19) has been synthesized from 4-methyl- 1,2,3-thiadiazole-5-carbonyl chloride as the starting material, and its structure was characterized by proton Nuclear Magnetic Resonance (1H NMR), Infra Red Spectroscopy (IR), high-resolution mass spectroscopy (HRMS), and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group Pi with a = 6.0780(8), b = 11.3760(14), c = 12.1440(18) A, α = 96.887(7), β = 91.027(12), γ= 104.252(13)°, Z = 2, V= 806.98(19)A3, Dc = 1.840 g/cm3, μ= 0.601 mm-1, F(000) = 448, R = 0.0450 and wR = 0.0869. X-ray analysis indicates that the 1,2,3-thiadiazole ring is not coplanar with the phenyl ring, and the dihedral angle is 33.57°. Two intermolecular hydrogen bonds N(2)-H…O(1 ), S(1 )…H-C(11), and three weak intermolecular interactions, C(11)…O(1), N(1)…O(2) and S…O(1), are observed. The bioassay results indicate that the title compound has good insecticidal activity against Culex pipiens pallens and good induction activity for tobacco against tobacco mosaic virus which is equal to that of TDL.展开更多
The title complex [AgL(NO3)]2 1, where L = 2-acetamido-5-methyl-1,3,4-thiadiazole, was prepared from the reaction of 2-acetamido-5-methyl-1,3,4-thiadiazole with AgNO3 at room temperature and its structure has been d...The title complex [AgL(NO3)]2 1, where L = 2-acetamido-5-methyl-1,3,4-thiadiazole, was prepared from the reaction of 2-acetamido-5-methyl-1,3,4-thiadiazole with AgNO3 at room temperature and its structure has been determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group P2t/c with a = 12.5454(8), b = 11.9672(12), c = 6.8925(6) A, β = 98.468(2)°. V= 1023.51(15) A^3, Mr= 3127.08, Dc = 2.123 g/cm^3, Z= 4, μ(MoKoσ) = 2.174 mm^-1, F(000) = 640, R = 0.0259 and wR = 0.0580 for 1787 observed reflections with I 〉 2σ(I). Complex 1 self-assembls into a quasi-three-dimensional network consisting of adjacent dimers through intermolecular Ag...O weak interactions.展开更多
The title compound 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole 5(C26H18Cl2N8S4) was synthesized, and its structure was confirmed by 1H NMR, MS and elemental analyses and X-ray diffraction...The title compound 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole 5(C26H18Cl2N8S4) was synthesized, and its structure was confirmed by 1H NMR, MS and elemental analyses and X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 9.452(4), b = 12.335(4), c = 13.017(5) A, α = 90.624(5), β = 110.541(5), γ =104.879(4)°, Dc = 1.561 g/cm3, Z = 2, V = 1364.9(9) A3, F(000) = 656, the final R = 0.0300 and w R = 0.0635 for 4206 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 activities to be 9.82%, 44.44% and 20.00%, respectively.展开更多
A new series of N^1-acetylamino-(5-alkyl/aryl- 1,3,4-thiadiazole-2-yl)-5-fluorouracil derivatives were designed and synthesized. These compounds have not been reported in literature, and their structure chemical wer...A new series of N^1-acetylamino-(5-alkyl/aryl- 1,3,4-thiadiazole-2-yl)-5-fluorouracil derivatives were designed and synthesized. These compounds have not been reported in literature, and their structure chemical were confirmed by IR, ^1H NMR and MS (HRMS). The results of antitumor inhibitory activity test showed that some compounds possess more potent antitumor inhibitory activity than 5-fluorouracil.展开更多
In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l...In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l,3,4-thiadiazol-2-yl}carba- mothioyl)-2/3/4-substitutedbenzamide were designed, synthesized and evaluated for their anticonvulsant activity. The findings of the present studies confirmed that the pharmacophore model with four binding sites is crucial for anticonvulsant activity. Structure-activity relationships among synthesized compounds were also established.展开更多
Two novel cobalt(Ⅱ) compounds were obtained and characterized by X-ray sing- le-crystal diffraction, IR, 1H NMR and elemental analysis. Compound 1 crystallizes in monoclinic, space group P21/n, with a = 18.046(4)...Two novel cobalt(Ⅱ) compounds were obtained and characterized by X-ray sing- le-crystal diffraction, IR, 1H NMR and elemental analysis. Compound 1 crystallizes in monoclinic, space group P21/n, with a = 18.046(4), b = 11.335(3), c = 19.157(5)A, β = 92.707(3)°, Z = 4, V = 3914.4(16) A3, Mr = 968.56, Dc = 1.644 g/cm3, μ = 1.378 mm^-1, F(000) = 1960, the final R = 0.0367 and wR = 0.0895. The crystal of compound 2 is of monoclinic, space group P211c with a = 8.7253(10), b = 10.9031(13), c = 18.235(2)A,β = 93.2210(10)°, Z = 4, V = 1732.0(3)A3, Mr = 464.21, Dc = 1.780 g/cm3,μ = 1.560 mm-1, F(000) = 932, the final R = 0.0322 and wR = 0.0743.展开更多
By ring-closure of 1-nicotinyl-4-arylthiosemicarbazides under the catalysis of concentrated sulfuric acid or mercuric acetate, a series of 2-(3-pyridyl)-5-arylarnino-1,3,4-thiadiazoles and 2-(3-pyridyl)-5-ary-lamino-1...By ring-closure of 1-nicotinyl-4-arylthiosemicarbazides under the catalysis of concentrated sulfuric acid or mercuric acetate, a series of 2-(3-pyridyl)-5-arylarnino-1,3,4-thiadiazoles and 2-(3-pyridyl)-5-ary-lamino-1,3,4-oxadiazoles were synthesized, respectively. All the products were subjected to testing of biological activity. Furthermore, the IR, 1H NMR and MS spectral properties of these new compounds were studied in details and some significant conclusions were drawn.展开更多
Three novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles were designed,synthesized and characterized by IR,NMR and APCI-MS.3-o-Fluorophenyl-6-(4-decarboxydehydroabietyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(6a,C28H3...Three novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles were designed,synthesized and characterized by IR,NMR and APCI-MS.3-o-Fluorophenyl-6-(4-decarboxydehydroabietyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(6a,C28H31FN4S) was structurally determined by single-crystal X-ray diffraction.The crystal belongs to the orthorhombic system,space group P212121 with a=6.0153(14),b=12.2577(19),c=34.055(3)A,V=2511.0(7)A^3,Z=4,Mr=474.63,Dc=1.255Mg/m^3,λ=0.71073 A,μ(MoKα)=0.160 mm^-1,F(000)=1008,the final R=0.0555 and wR=0.1248 for 3094 observed reflections with I〉2σ(I).There are six rings in the crystal structure of the title compound.The dihedral angle between 1,2,4-triazole and 1,3,4-thiadiaole rings is 1.4o,and that between 1,2,4-triazole and benzene ring D 25.5o.展开更多
The compound 3,6-bis(4-methyl-1,2,3-thiadiazol-5-yl)-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole(C9H6N8S3,Mr = 322.40) has been synthesized by the reaction of 4-amino-3-(4-methyl-1,2,3-thiadiazolyl)-5-mercapto-1,2,...The compound 3,6-bis(4-methyl-1,2,3-thiadiazol-5-yl)-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole(C9H6N8S3,Mr = 322.40) has been synthesized by the reaction of 4-amino-3-(4-methyl-1,2,3-thiadiazolyl)-5-mercapto-1,2,4-triazole with 4-methyl-1,2,3-thiadiazol-5-carboxylic acid and phosphorus oxychloride,and its structure was characterized by IR,1H NMR,EI-MS,elemental analysis and single-crystal X-ray diffraction.The crystal of the title compound belongs to monoclinic,space group C2/c with a = 2.0053(4),b = 1.3081(3), c = 1.0556(2) nm, β = 112.69(3)°,Z = 4, V= 2.5548(9) nm^3, Dc = 1.676 g/cm^3, μ= 0.582 mm^-1, F(000) = 1312, R = 0.0546 and wR = 0.1523. X-ray analysis indicates that all rings are essentially planar in this molecule, and an intermolecular hydrogen bond C(9)-H(9)…N(2) and weak intramolecular interactions between S(1)…N(7), S(3)…N(1) and S(2)…N(4) are observed.展开更多
The crystal structure of the title compound, 2-isobutyl-6-(2?4?dichlorophenyl)- imidazo[2,1-b]-1,3,4-thiadiazole (C14H13Cl2N3S, Mr = 326.23), has been synthesized by the treatment of 2-amino-5-isobutyl-1,3,4-thiadiazo...The crystal structure of the title compound, 2-isobutyl-6-(2?4?dichlorophenyl)- imidazo[2,1-b]-1,3,4-thiadiazole (C14H13Cl2N3S, Mr = 326.23), has been synthesized by the treatment of 2-amino-5-isobutyl-1,3,4-thiadiazole with a-chloroaceto-2,4-dichlorophenone and determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 12.483(7), b = 8.420(4), c = 14.998(8) ? b = 105.770(10)? V = 1517.0(14) 3, Z = 4, Dc = 1.428 g/cm3, S = 0.902, m(MoKa) = 0.558 mm-1, F (000) = 672, R = 0.0579 and wR = 0.1186. The X-ray analytic results showed that all ring atoms in the imidazothiadiazole moiety are almost coplanar. The dihedral angel between the phenyl group and hetero-cycle is 16.8(0.2)?展开更多
基金supported by the U.S.Department of Energy,Office of Basic Energy Sciences,Division of Materials Science and Engineering under award number DE-SC0005397.
文摘Organosulfur materials are a sustainable alternative to the present-day layered oxide cathodes in lithium-based batteries.One such organosulfur material that was intensely explored from the 1990s to early 2010s is 2,5-dimercapto-1,3,4-thiadiazole(DMCT).However,research interest declined as the electrode reactions with DMCT were assumed to be too sluggish to be practical.Armed with the advances in metal-sulfur batteries,we revisit DMCT-based materials in the form of poly[tetrathio-2,5-(1,3,4-thiadiazole)],referred to as pDMCT-S.With an appropriate choice of electrode design and electrolyte,pDMCT-S cathode paired with a Li-metal anode shows a capacity of 715 mA h g^(-1)and a Coulombic efficiency of 97.7%at a C/10 rate,thus quelling the concerns of sluggish reactions.Surprisingly,pDMCT-S shows significantly improved long-term cyclability compared to a sulfur cathode.Investigations into the origin of the stability reveals that the discharge product Li-DMCT in its mesomeric form can strongly bind to polysulfides,preventing their dissolution into the electrolyte and shuttling.This unique mechanism solves a critical problem faced by sulfur cathodes.Encouragingly,this mechanism results in a stable performance of pDMCT-S with Na-metal cells as well.This study opens the potential for exploring other organic materials that have inherent polysulfide sequestering capabilities,enabling long-life metal-sulfur batteries.
基金support from the Natural Science Foundation of Gansu Province(No.3ZS061- A25-019)the Scientific Research fund of Gansu Provincial Education Department(No.0601-25)
基金funded by National Natural Science Foundation of China(No.21002090)the National Key Technologies R&D Program(2011BAE06B03-01)
文摘5-(4-Cyclopropyl-5-((3-fluorobenzyl)sulfonyl)-4H-1,2,4-triazol-3-yl)-4-methyl-1,2,3-thiadiazole was synthesized and recrystallized from Et OH. The compound was characterized by ^1H NMR,MS,elemental analysis and X-ray diffraction. The structure-active relationship and the antifungal activity based on density functional theory calculation(DFT) and antifungal activities were investigated. The compound crystallizes in the monoclinic space group P121/n1 with a = 8.929(3),b=12.715(4),c=15.161(5) A°,β = 106.142(3)o,V = 1653.3(9) A°3,Z = 4 and R = 0.0393 for 3930 observed reflections with I 〉 2σ(I). Theoretical calculation of the title compound was carried out with B3LYP/6-31G(d,p). The full geometry optimization was carried out using the 6-31G(d,p) basis set.The frontier orbital energy and atomic net charges were discussed. The observed results of the compound have been compared with theoretical results and the experimental data show good agreement with the calculated values. The compound exhibits good antifungal activity.
基金This work was supported by the 973 Program of the MOST (001CB108906) and the Natural Science Foundation of Fujian Province (2005HZ01-1)
文摘The title compound, [HgI2(C12H8N4S)], has been synthesized and characterized by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 14.086(2), b = 6.0365(6), c = 20.286(2)°A,β= 108.818(5)°, V = 1632.7(3)°A^3, Mr = 694.67, Z = 4, D, = 2.826 g/cm^3,μ= 13.331 mm^-1, F(000) = 1240, S = 1.108, the final R = 0.0438 and wR = 0.0934 for 3085 observed reflections (I〉 2σ(I)). The Hg(Ⅱ) atom is coordinated by two 2,5-bis(4-pyridyl)-1,3,4-thiadiazole (L) molecules and two iodine anions in a distorted tetrahedral coordination geometry. Mercury atoms are linked by the organic ligands to form a one-dimensional zigzag chain. It is noteworthy that such 1D zigzag chains are extended into a two-dimensional double layer framework through I…I interactions
基金funded in part by the NNSFC (Nos. 20872071, 20672062 and 20911120069)the NSF of Tianjin (10JCZDJC17500)+3 种基金the National Key Project for Basic Research (2010CB126105)the Foundation of Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture (MOA) (No. MOAPCA200903)the Russian Foundation for Basic Research (grant numbers RFBR 08-03-00376a and RFBR/NNSF 08-03-92208a)the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology (No. 201002250)
文摘The title compound N-tert-butyl-N-(4-methyl-1,2,3-thiadiazole)-5-yl-N'-(4-me-thyl-1,2,3-thiadiazole)-5-formyl-N'-3,5-dichloropyrid-2-yl-diacylhydrazines (C18H17Cl2N7O3S2, Mr = 514.41) has been synthesized by the reaction of N-tert-butyl-N'-3,6-dichloropyridine-2-formyl hydrazine with 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride and triethylamine, and its structure was characterized by 1H NMR, HR MS, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group C2/c with a = 27.726(8), b = 11.045(3), c = 14.507(4)A, β = 96.758(4)°, Z = 8, V = 4412(2) A^3, Dc = 1.549 g/cm^3, μ = 0.521 mm^-1, F(000) = 2112, R = 0.0405 and wR = 0.1153. X-ray analysis indicates that all rings are non-planar in this molecule. The bioassay results indicate that both the title compound and the positive control RH-5992 have weak fungicide activities, while the title compound has good insecticidal activity against Plutella xylostella L. and no insecticidal activity against Culex pipiens pallens.
基金Supported by the National Natural Science Foundation of China (Nos. 20872071 and 20911120069)the Natural Science Foundation of Tianjin (10JCZDJC17500)+2 种基金the National Key Project for Basic Research (2010CB126105)the Key Laboratory of Pesticide Chemistry and Application,Ministry of Agriculture (MOA) (No. MOAPCA200903)the Russian Foundation for Basic Research (grant numbers RFBR 08-03-00376 a and RFBR/NNSF 08-03-92208 a)
文摘The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate (C 14 H 10 N 2 O 2 S,M r=270.31) was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its structure was characterized by IR,1 H NMR,high-resolution mass spectrometry and single-crystal X-ray diffraction.The crystal belongs to orthorhombic,space group Pbcn with a=23.475(5),b=9.6640(19),c=10.814(2),β=90.00°,Z=8,V=2453.2(9) 3,M r=270.30,D c=1.464 g/cm 3,μ=0.262 mm-1,F(000)=1120,R=0.0444 and wR=0.1099.X-ray analysis revealed that the thiadiazole and naphthalene rings were non-planar,while the thiadiazole ring and the ester group were essentially planar,and two intermolecular hydrogen bonds C(6) H(6)···O(1) and C(14) H(14)···O(1) were observed.The preliminary biological test showed that the title compound had antifungal and antivirus activities against tobacco mosaic virus.
文摘A facile one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles was achieved by ultrasonic irradiation of a mixture of 1-naphthylacetyl chloride, NH4CNS, CH2Cl2 and PEG-400 for 1.5 h at 10–20 °C and subsequent irradiation for 1.5 h in the presence of N-arylglycine hydrazides. This method requires short time and gives thiadiazoles in high yields.
基金funded in part by the NNSFC (20872071), the NSF of Tianjin (10JCZDJC17500)the National Key Project for Basic Research (2010CB126105)+2 种基金National Key Technology Research and Development Program (2011BAE06B02 and 2011BAE06B05)the Foundation of Achievements Transformation and Application of Tianjin Agricultural Science and Technology (201002250)Tianjin Key Technology Research and Development Program (11ZCGYNC00100)
文摘The title compound N-(tert-butyl)-N'-(2-(4-chlorophenyl)acetyl)-5-methyl-1,2,3-thiadiazole-4-carbohydrazide (C16H19ClN4NaO2S, Mr = 366.86) has been synthesized, and its structure was characterized by IR, 1H NMR, H RMS and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group Pī with a = 8.464(2), b = 10.192(2), c = 11.757(2), α = 68.48(3), β = 76.31(3), γ = 80.86(3)°, Z = 2, V = 2024.6(10) 3, Dc = 1.333 g/cm3, μ = 0.339 mm-1, F(000) = 384, R = 0.0450 and wR (Ⅰ 〉 2σ(Ⅰ)) = 0.1234. X-ray analysis indicates one N-H…N intermolecular hydrogen bond and no π-π stacking interactions are observed in this crystal structure. The preliminary biological test shows that the title compound has fungicidal activity and antivirus activities against tobacco mosaic virus.
基金funded in part by grants from the National Natural Science Foundation of China (20872071)the Natural Science Foundation of Tianjin (10JCZDJC17500)+3 种基金the National Key Project for Basic Research (2010CB126105)the National Key Technology Research and Development Program (2011BAE06B02)the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology(201002250)Tianjin Key Technology Research and Development Program (11ZCGYNC00100)
文摘The title compound N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N'-3,5-dichloro-4- (1,1,2,2- tetrafluoroethoxyl)phenyl urea (C13H8Cl2F4N4O3S, Mr = 447.19) has been synthesized from 4-methyl- 1,2,3-thiadiazole-5-carbonyl chloride as the starting material, and its structure was characterized by proton Nuclear Magnetic Resonance (1H NMR), Infra Red Spectroscopy (IR), high-resolution mass spectroscopy (HRMS), and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group Pi with a = 6.0780(8), b = 11.3760(14), c = 12.1440(18) A, α = 96.887(7), β = 91.027(12), γ= 104.252(13)°, Z = 2, V= 806.98(19)A3, Dc = 1.840 g/cm3, μ= 0.601 mm-1, F(000) = 448, R = 0.0450 and wR = 0.0869. X-ray analysis indicates that the 1,2,3-thiadiazole ring is not coplanar with the phenyl ring, and the dihedral angle is 33.57°. Two intermolecular hydrogen bonds N(2)-H…O(1 ), S(1 )…H-C(11), and three weak intermolecular interactions, C(11)…O(1), N(1)…O(2) and S…O(1), are observed. The bioassay results indicate that the title compound has good insecticidal activity against Culex pipiens pallens and good induction activity for tobacco against tobacco mosaic virus which is equal to that of TDL.
文摘The title complex [AgL(NO3)]2 1, where L = 2-acetamido-5-methyl-1,3,4-thiadiazole, was prepared from the reaction of 2-acetamido-5-methyl-1,3,4-thiadiazole with AgNO3 at room temperature and its structure has been determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group P2t/c with a = 12.5454(8), b = 11.9672(12), c = 6.8925(6) A, β = 98.468(2)°. V= 1023.51(15) A^3, Mr= 3127.08, Dc = 2.123 g/cm^3, Z= 4, μ(MoKoσ) = 2.174 mm^-1, F(000) = 640, R = 0.0259 and wR = 0.0580 for 1787 observed reflections with I 〉 2σ(I). Complex 1 self-assembls into a quasi-three-dimensional network consisting of adjacent dimers through intermolecular Ag...O weak interactions.
基金funded by the National Natural Science Foundation of China(No.21002090)the Key Innovation Team of Science and Technology in Zhejiang Province(2010R50018-06)the National Key Technologies R&D Program(2011BAE06B03-01)
文摘The title compound 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole 5(C26H18Cl2N8S4) was synthesized, and its structure was confirmed by 1H NMR, MS and elemental analyses and X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 9.452(4), b = 12.335(4), c = 13.017(5) A, α = 90.624(5), β = 110.541(5), γ =104.879(4)°, Dc = 1.561 g/cm3, Z = 2, V = 1364.9(9) A3, F(000) = 656, the final R = 0.0300 and w R = 0.0635 for 4206 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 activities to be 9.82%, 44.44% and 20.00%, respectively.
文摘A new series of N^1-acetylamino-(5-alkyl/aryl- 1,3,4-thiadiazole-2-yl)-5-fluorouracil derivatives were designed and synthesized. These compounds have not been reported in literature, and their structure chemical were confirmed by IR, ^1H NMR and MS (HRMS). The results of antitumor inhibitory activity test showed that some compounds possess more potent antitumor inhibitory activity than 5-fluorouracil.
文摘In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l,3,4-thiadiazol-2-yl}carba- mothioyl)-2/3/4-substitutedbenzamide were designed, synthesized and evaluated for their anticonvulsant activity. The findings of the present studies confirmed that the pharmacophore model with four binding sites is crucial for anticonvulsant activity. Structure-activity relationships among synthesized compounds were also established.
文摘Two novel cobalt(Ⅱ) compounds were obtained and characterized by X-ray sing- le-crystal diffraction, IR, 1H NMR and elemental analysis. Compound 1 crystallizes in monoclinic, space group P21/n, with a = 18.046(4), b = 11.335(3), c = 19.157(5)A, β = 92.707(3)°, Z = 4, V = 3914.4(16) A3, Mr = 968.56, Dc = 1.644 g/cm3, μ = 1.378 mm^-1, F(000) = 1960, the final R = 0.0367 and wR = 0.0895. The crystal of compound 2 is of monoclinic, space group P211c with a = 8.7253(10), b = 10.9031(13), c = 18.235(2)A,β = 93.2210(10)°, Z = 4, V = 1732.0(3)A3, Mr = 464.21, Dc = 1.780 g/cm3,μ = 1.560 mm-1, F(000) = 932, the final R = 0.0322 and wR = 0.0743.
文摘By ring-closure of 1-nicotinyl-4-arylthiosemicarbazides under the catalysis of concentrated sulfuric acid or mercuric acetate, a series of 2-(3-pyridyl)-5-arylarnino-1,3,4-thiadiazoles and 2-(3-pyridyl)-5-ary-lamino-1,3,4-oxadiazoles were synthesized, respectively. All the products were subjected to testing of biological activity. Furthermore, the IR, 1H NMR and MS spectral properties of these new compounds were studied in details and some significant conclusions were drawn.
基金Supported by the Foundation of 100 Young and Middle-aged Discipline Leaders of Guangxi Province in the 21st century (No 2004219)the Natural Science Foundation of Guangxi Province (No 0731054)
文摘Three novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles were designed,synthesized and characterized by IR,NMR and APCI-MS.3-o-Fluorophenyl-6-(4-decarboxydehydroabietyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(6a,C28H31FN4S) was structurally determined by single-crystal X-ray diffraction.The crystal belongs to the orthorhombic system,space group P212121 with a=6.0153(14),b=12.2577(19),c=34.055(3)A,V=2511.0(7)A^3,Z=4,Mr=474.63,Dc=1.255Mg/m^3,λ=0.71073 A,μ(MoKα)=0.160 mm^-1,F(000)=1008,the final R=0.0555 and wR=0.1248 for 3094 observed reflections with I〉2σ(I).There are six rings in the crystal structure of the title compound.The dihedral angle between 1,2,4-triazole and 1,3,4-thiadiaole rings is 1.4o,and that between 1,2,4-triazole and benzene ring D 25.5o.
基金supported by the National Natural Science Foundation of China (Nos 20672062 and 20872071)the Natural Science Foundation of Tianjin (No 07JCYBJC01200)+1 种基金the International Collaboration Program of the National Natural Science Foundation of China (No 20911120069)International Collaboration Program of Tianjin on Science and Technology (No 07ZCGHHZ01400)
文摘The compound 3,6-bis(4-methyl-1,2,3-thiadiazol-5-yl)-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole(C9H6N8S3,Mr = 322.40) has been synthesized by the reaction of 4-amino-3-(4-methyl-1,2,3-thiadiazolyl)-5-mercapto-1,2,4-triazole with 4-methyl-1,2,3-thiadiazol-5-carboxylic acid and phosphorus oxychloride,and its structure was characterized by IR,1H NMR,EI-MS,elemental analysis and single-crystal X-ray diffraction.The crystal of the title compound belongs to monoclinic,space group C2/c with a = 2.0053(4),b = 1.3081(3), c = 1.0556(2) nm, β = 112.69(3)°,Z = 4, V= 2.5548(9) nm^3, Dc = 1.676 g/cm^3, μ= 0.582 mm^-1, F(000) = 1312, R = 0.0546 and wR = 0.1523. X-ray analysis indicates that all rings are essentially planar in this molecule, and an intermolecular hydrogen bond C(9)-H(9)…N(2) and weak intramolecular interactions between S(1)…N(7), S(3)…N(1) and S(2)…N(4) are observed.
基金The project was supported by NNSFC (20172031 29832050) the NSF of shandong province (Y2003B01) and the Fund for the Doctoral Program of Higher Education
文摘The crystal structure of the title compound, 2-isobutyl-6-(2?4?dichlorophenyl)- imidazo[2,1-b]-1,3,4-thiadiazole (C14H13Cl2N3S, Mr = 326.23), has been synthesized by the treatment of 2-amino-5-isobutyl-1,3,4-thiadiazole with a-chloroaceto-2,4-dichlorophenone and determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 12.483(7), b = 8.420(4), c = 14.998(8) ? b = 105.770(10)? V = 1517.0(14) 3, Z = 4, Dc = 1.428 g/cm3, S = 0.902, m(MoKa) = 0.558 mm-1, F (000) = 672, R = 0.0579 and wR = 0.1186. The X-ray analytic results showed that all ring atoms in the imidazothiadiazole moiety are almost coplanar. The dihedral angel between the phenyl group and hetero-cycle is 16.8(0.2)?