The crystal structure of the title compound 3 (4 Chloro 3 ethyl 1 methyl 1H pyrazol 5 yl) 6 (E)phenylvinyltriazolo[3,4 b] 1,3,4 thiadiazole (C 17 H 15 ClN 6S, M r =370.87) was determined by...The crystal structure of the title compound 3 (4 Chloro 3 ethyl 1 methyl 1H pyrazol 5 yl) 6 (E)phenylvinyltriazolo[3,4 b] 1,3,4 thiadiazole (C 17 H 15 ClN 6S, M r =370.87) was determined by single crystal X ray diffraction. The crystal is monoclinic, space group P2 1/n , a=10.862(2), b=11.541(2), c=14\^994(3), β=108.41(3)°, V=1783(1), Z=4, D x =1.381 g/cm -3 , μ =0.3361 mm -1 , and F (000)=768. The results confirmed that the title compound belongs to type E of stereochemistry. The dihedral angle between triazole and 1,3,4 thiadiaole ring is 3° and the torsion angle between 1,3,4 thiadiazole and pyrazole ring is 134.0°.展开更多
6/3-(4-Chlorophenyl)-s-triazolo[3, 4-b][1, 3, 4]thiadiazoles (2,a-e) and (Sa-e) were synthesized respectively by intermolecular cyclization of 5-aryl / 4-chlorophenyl-4-amino-3- mercapto-1, 2, 4-triazoles (la-e...6/3-(4-Chlorophenyl)-s-triazolo[3, 4-b][1, 3, 4]thiadiazoles (2,a-e) and (Sa-e) were synthesized respectively by intermolecular cyclization of 5-aryl / 4-chlorophenyl-4-amino-3- mercapto-1, 2, 4-triazoles (la-e) and (4) with 4-chlorobenzoic acid / aryl acids, which were condensed with piperazine under phase transfer catalyst TBAB to yield the corresponding free bases of monopiperazine derivatives and followed to form water-soluble salts (3a-e) and (6a-e) with hydrochloric acid in good yields. The in vitro biological results showed that piperazine group conjugated with the above fused heterocycles played an important role in antibacterial activity. The structures of novel compounds were confirmed by IR, 'H NMR, MS and elemental analysis.展开更多
In recent years, fused heterocycles have been reported to possess important properties in synthesis and pharmacology. Especially, s-triazolo, 3,4-thiadiazole derivatives have been attracting much attention for chemist...In recent years, fused heterocycles have been reported to possess important properties in synthesis and pharmacology. Especially, s-triazolo, 3,4-thiadiazole derivatives have been attracting much attention for chemists and pharmacologists because they show broad spectra of biological activities, such as antifungal, antibacterial, hy-展开更多
The title compound 3-benzyl-6-trichloromethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole I (C11HTC13N4S, Mr = 333.62) has been synthesized, and its structure was determined by elemental analyses, IR, ^1H NMR, ^13C NMR...The title compound 3-benzyl-6-trichloromethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole I (C11HTC13N4S, Mr = 333.62) has been synthesized, and its structure was determined by elemental analyses, IR, ^1H NMR, ^13C NMR, and X-ray diffractions. The crystal is of triclinic, space group P1^-, with a = 5.898(3), b = 10.510(4), c = 11.580(5) A, α = 74.936(7), β= 75.476(7), γ = 79.647(7)°, V= 665.9(5)/A^3, F(000) = 336, Z= 2, Dc = 1.664 g/cm^3, 2 = 0.71073A, p = 0.834 mm^-1, the final R = 0.0605 and wR = 0.0900. The secondary bonding interactions (SBIs) S…N and π-π stacking interactions are found in the crystal structure and they link the molecules into a three-dimensional network.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
本文报道1-(5-二茂铁基-1,3,4-噻二唑-2-基)哌啶-2-酮(1)的合成。首先,在乙酸催化下,二茂铁甲醛(2)和氨基硫脲(3)反应得到二茂铁亚胺基硫脲衍生物(4)。然后,在三氯化铁作用下,中间体4发生关环反应得到5-二茂铁基-1,3,4-噻二唑-2-胺(5)...本文报道1-(5-二茂铁基-1,3,4-噻二唑-2-基)哌啶-2-酮(1)的合成。首先,在乙酸催化下,二茂铁甲醛(2)和氨基硫脲(3)反应得到二茂铁亚胺基硫脲衍生物(4)。然后,在三氯化铁作用下,中间体4发生关环反应得到5-二茂铁基-1,3,4-噻二唑-2-胺(5)。中间体5再与5-溴戊酰氯(6)发生N-酰基化反应得到5-溴-N-(5-二茂铁基-1,3,4-噻二唑-2-基)戊酰胺(7)。最后,在碱性条件下,中间体7发生分子内关环反应得到目标化合物(1)。中间体及产物结构经1 H NMR、13 C NMR和ESI-MS表征,产物1结构进一步通过X-单晶衍射确证。然后分别考察了中间体5及产物1收率的主要影响因素,确定中间体5合成的适宜条件为:三氯化铁的用量为n(三氯化铁)∶n(中间体4)=4∶1,反应温度80℃,反应时间为15 h,在该条件下,中间体5的收率达到61.9%;确定产物1合成的适宜条件为:反应溶剂为二氧六环,物料比为n(DIEA)∶n(6)∶(5)=3.0∶1.2∶1.0、反应温度为80℃,反应时间为4 h,在该条件下,产物1收率达到68.4%。展开更多
Benzyl 4 amino 5 mercapto 1,2,4 triazole reacted with aromatic acids in the presence of phosphorus oxychloride, yielding a series of new compounds, i.e. , 3 benzyl 6 aryl 1,2,4 triazolothiadiazoles, each of which has ...Benzyl 4 amino 5 mercapto 1,2,4 triazole reacted with aromatic acids in the presence of phosphorus oxychloride, yielding a series of new compounds, i.e. , 3 benzyl 6 aryl 1,2,4 triazolothiadiazoles, each of which has an active methylene at 3 position. The structures of all the title compounds were confirmed by elementary analysis, IR, 1H NMR and 13 C NMR spectra.展开更多
By the condensation of 2,6-bis(4-amino-5-mercapto-[1,2,4]-triazoles-2)pyridine with aromatic acid in the presence of phosphorus oxychloride. Compounds of 2,6-bis(6-aryl-[1,2,4]-triazolo[3,4-b][1,3,4]-thiadiazole-3...By the condensation of 2,6-bis(4-amino-5-mercapto-[1,2,4]-triazoles-2)pyridine with aromatic acid in the presence of phosphorus oxychloride. Compounds of 2,6-bis(6-aryl-[1,2,4]-triazolo[3,4-b][1,3,4]-thiadiazole-3-yl)pyridines were synthesized. Their structures were confirmed by IR, ^1H NMR spectroscopies and elemental analysis. Their electrochemical behavior and cyclic voltammogram also were be studied. The results showed that they have high ionization potentials and good affinity.展开更多
文摘The crystal structure of the title compound 3 (4 Chloro 3 ethyl 1 methyl 1H pyrazol 5 yl) 6 (E)phenylvinyltriazolo[3,4 b] 1,3,4 thiadiazole (C 17 H 15 ClN 6S, M r =370.87) was determined by single crystal X ray diffraction. The crystal is monoclinic, space group P2 1/n , a=10.862(2), b=11.541(2), c=14\^994(3), β=108.41(3)°, V=1783(1), Z=4, D x =1.381 g/cm -3 , μ =0.3361 mm -1 , and F (000)=768. The results confirmed that the title compound belongs to type E of stereochemistry. The dihedral angle between triazole and 1,3,4 thiadiaole ring is 3° and the torsion angle between 1,3,4 thiadiazole and pyrazole ring is 134.0°.
基金This project was supported by the State Basic Research and Development Project(No.G1998051112).
文摘6/3-(4-Chlorophenyl)-s-triazolo[3, 4-b][1, 3, 4]thiadiazoles (2,a-e) and (Sa-e) were synthesized respectively by intermolecular cyclization of 5-aryl / 4-chlorophenyl-4-amino-3- mercapto-1, 2, 4-triazoles (la-e) and (4) with 4-chlorobenzoic acid / aryl acids, which were condensed with piperazine under phase transfer catalyst TBAB to yield the corresponding free bases of monopiperazine derivatives and followed to form water-soluble salts (3a-e) and (6a-e) with hydrochloric acid in good yields. The in vitro biological results showed that piperazine group conjugated with the above fused heterocycles played an important role in antibacterial activity. The structures of novel compounds were confirmed by IR, 'H NMR, MS and elemental analysis.
文摘In recent years, fused heterocycles have been reported to possess important properties in synthesis and pharmacology. Especially, s-triazolo, 3,4-thiadiazole derivatives have been attracting much attention for chemists and pharmacologists because they show broad spectra of biological activities, such as antifungal, antibacterial, hy-
基金supported by the Natural Science Foundation of Zhejiang Province (No. M203149)
文摘The title compound 3-benzyl-6-trichloromethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole I (C11HTC13N4S, Mr = 333.62) has been synthesized, and its structure was determined by elemental analyses, IR, ^1H NMR, ^13C NMR, and X-ray diffractions. The crystal is of triclinic, space group P1^-, with a = 5.898(3), b = 10.510(4), c = 11.580(5) A, α = 74.936(7), β= 75.476(7), γ = 79.647(7)°, V= 665.9(5)/A^3, F(000) = 336, Z= 2, Dc = 1.664 g/cm^3, 2 = 0.71073A, p = 0.834 mm^-1, the final R = 0.0605 and wR = 0.0900. The secondary bonding interactions (SBIs) S…N and π-π stacking interactions are found in the crystal structure and they link the molecules into a three-dimensional network.
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.
文摘本文报道1-(5-二茂铁基-1,3,4-噻二唑-2-基)哌啶-2-酮(1)的合成。首先,在乙酸催化下,二茂铁甲醛(2)和氨基硫脲(3)反应得到二茂铁亚胺基硫脲衍生物(4)。然后,在三氯化铁作用下,中间体4发生关环反应得到5-二茂铁基-1,3,4-噻二唑-2-胺(5)。中间体5再与5-溴戊酰氯(6)发生N-酰基化反应得到5-溴-N-(5-二茂铁基-1,3,4-噻二唑-2-基)戊酰胺(7)。最后,在碱性条件下,中间体7发生分子内关环反应得到目标化合物(1)。中间体及产物结构经1 H NMR、13 C NMR和ESI-MS表征,产物1结构进一步通过X-单晶衍射确证。然后分别考察了中间体5及产物1收率的主要影响因素,确定中间体5合成的适宜条件为:三氯化铁的用量为n(三氯化铁)∶n(中间体4)=4∶1,反应温度80℃,反应时间为15 h,在该条件下,中间体5的收率达到61.9%;确定产物1合成的适宜条件为:反应溶剂为二氧六环,物料比为n(DIEA)∶n(6)∶(5)=3.0∶1.2∶1.0、反应温度为80℃,反应时间为4 h,在该条件下,产物1收率达到68.4%。
基金Supported by the National Natural Science Foundation of Chinathe University Backbone Teachers Foundation of theEducation Ministry of Chinaand Zhejiang Province Education Department
文摘Benzyl 4 amino 5 mercapto 1,2,4 triazole reacted with aromatic acids in the presence of phosphorus oxychloride, yielding a series of new compounds, i.e. , 3 benzyl 6 aryl 1,2,4 triazolothiadiazoles, each of which has an active methylene at 3 position. The structures of all the title compounds were confirmed by elementary analysis, IR, 1H NMR and 13 C NMR spectra.
文摘By the condensation of 2,6-bis(4-amino-5-mercapto-[1,2,4]-triazoles-2)pyridine with aromatic acid in the presence of phosphorus oxychloride. Compounds of 2,6-bis(6-aryl-[1,2,4]-triazolo[3,4-b][1,3,4]-thiadiazole-3-yl)pyridines were synthesized. Their structures were confirmed by IR, ^1H NMR spectroscopies and elemental analysis. Their electrochemical behavior and cyclic voltammogram also were be studied. The results showed that they have high ionization potentials and good affinity.