Synthesis and Crystal Structure of 5-[（1H-1,2,4-Triazol-1- yl）methyl]-4-（2,3-dimethoxybenzylideneamino）-2- 2H-1,2,4-triazole-3（4H）-thione Monohydrate

1 INTRODUCTION Heterocyclic compounds bearing the 1,2,4-tri- azole moiety have attracted considerable attention over the past few decades since they exhibit some fungicidal activities against Puccinia recondite and applications in the field of root-growth regu- lation[1~3]. Meanwhile, 4-amino-5-mercapto-1,2, 4-triazole moiety has great versatility in fusing tovarious ring systems and possesses a broad spec- trum of biological activities[4, 5]. In our con- tinuous work directed towards the…     

(Z)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮肟(5-芳基-1,3,4-噁二唑-2-基)甲基醚的合成和抑菌活性

以3,3-二甲基-1-（1H-1,2,4-三唑基）-2-丁酮肟为原料,经醚化、肼解及腙化3步反应得到（E）-N'-（取代苯亚甲基）-2-[（Z）-3,3-二甲基-1-（1H-1,2,4-三唑-1-基）丁基-2-亚甲氨氧基]乙酰肼（3a~3u）,化合物3与二乙酸碘苯（IBD）反应,合成了21个（Z）-3,3-二甲基-1-（1H-1,2,4-三唑-1-基）-2-丁酮肟-（5-芳基-1,3,4-噁二唑-2-基）甲基醚（4a~4u）,化合物4的化学结构经核磁共振谱、高分辨质谱和元素分析确证.采用单晶X射线衍射仪测定了化合物4c的晶体结构.抑菌活性测试结果表明,在500 mg/L浓度下,化合物4k,4f,4j和4n对纹枯病菌的防效率分别为70.9%,60.2%,60.0%和60.6%;在25 mg/L浓度下,化合物4b,4c,4d和4e对菌核病菌的抑制率为71.8%~76.9%.     

Structural study and thermal behavior of novel interaction product of 4-amino-5-(furan-2-yl)-4H-1,2,4-triazole-3-thione with molecular iodine

Abstract

As a part of investigation of thyreostatic activity of mercapto-substituted triazoles, the structure, spectroscopic properties of 4-amino-5-(furan-2-yl)-4H-1,2,4-triazole-3-thione were obtained. 4-amino-5-(furan-2-yl)-4H-1,2,4-triazole-3-thione forms steady charge-transfer complex in dilute chloroform solution, coordinating one iodine molecule (lgβ?=?3.47). The reaction product of 4-amino-5-(furan-2-yl)-4H-1,2,4-triazole-3-thione is presented by uncharged adduct: C₆H₆N₄OS·I₂. The crystal structure of the adduct was studied in detail by single crystal X-ray diffraction. The results of thermogravimetric analysis revealed the stability of adduct in a solid state at the temperature range 50–500?°C.     

Experimental,DFT and Theoretical Corrosion Study for 4-(((4-ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazole-3-yl)thio)methyl)-7,8-dimethyl-2H-chromen-2-one

In this work, 4-(((4-ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazole-3-yl)thio)methyl)-7,8-dimethyl-2H-chromen-2-one was synthesized by acetone-mediated condensation of 4-ethyle-5-(thiophen-2-yl)-4H-1,2,4-triazole-3-thiol and 4-(chloromethyl)-7,8-dimethyl-2H-chromen-2-one. The molecule results (3) were experimentally characterized using FT-IR, ¹H-, and ¹³C NMR spectroscopy. Density Functional Theory (B3LYP/cc-pVDZ) was used to investigate the ideal molecule structure, vibrational frequencies, and ¹H with ¹³C NMR (theoretically) chemical shifts. Theoretical and experimental spectroscopy results were compared and agreed with each other, which indicated the validity of the used developed molecular structure. The Dipole moment, hardness, softnes, electronegativity, electrophilicity index, nucleophilicity index, and chemical potential as electronic structural parameters linked to corrosion inhibition efficacy were investigated for the prepared compound. Furthermore, the fraction of transferred electrons was calculated to determine the interaction between the iron surface and organic molecules. The results indicated a favorable relationship between organic-based corrosion inhibitors and quantum chemical parameters processes. The corrosion inhibitors' behavior can be predicted without the need for experimental investigation.     

Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones

Russian Journal of Organic Chemistry - The addition of 5-(1,4-benzodioxan-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol to the C=C double bond of acrylonitrile, acrylamide, and ethyl acrylate afforded...     

Nonlinear optical and ferroelectric properties of a 3-D Cd(II) triazolate complex with a novel (6(3))2(6(10) x 8(5)) topology

A novel 3-D (3,6)-connected topological architecture, obtained by reacting Cd(ClO4)2 x 6H2O with Htrtr (Htrtr = 3-(1,2,4-triazole-4-yl)-1H-1,2,4-triazole) under solvothermal conditions, presents a non-centrosymmetric polar packing arrangement, resulting in a strong second harmonic generation (SHG) response and ferroelectric property.     

Preparation of aminotriazole-thione derivatives from n-aryl-n-carboxyethyl-β-alanines

Depending on the substituents in the aryl moiety, the fusion of N-aryl-N-ethoxycarbonyl-β-alanines with thiocarbohydrazide gives di- or monotriazole derivatives, namely, 4-amino-(2-{[2-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethyl]anilino}ethyl)-4,5-dihydro-1H-1,2,4-triazole-5-thiones, 1-[2-(4-amino- 5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethyl]-2,3-dihydroquinolin-4(1H)-ones, 4-amino-3-[2-(4-methylanilino))ethyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione and 4-amino-3-[2-(4-ethoxyanilino)-ethyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione. A ditriazolethione derivative was also obtained from the diethyl ester of N-ethoxycarbonyl-N-(4-ethoxyphenyl)- β-alanine.     

新型S(N)-β-D-葡萄糖苷-4-N-(取代邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑的合成及生物活性

在KOH/acetone体系中,4-N-(取代邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-3-硫酮(3a～3d)与溴-α-D-四乙酰葡萄糖发生Kenigs-Knorr反应,合成了8个未见报道的S(N)-β-D-乙酰葡萄糖苷,其结构经1H NMR、13C NMR、红外光谱及元素分析等确定.目标化合物的生物活性测试结果表明,它们对金黄色葡萄球菌、白色念珠菌和大肠杆菌均显示了较好的抑菌活性,其效果接近或优于对照药物三氯生和氟康唑的抑菌效能.其中,化合物2-N-(2’,3’,4’,6’-O-四乙酰基-β-D-吡喃葡萄糖基)-4-N-(3,5-二溴邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-3-硫酮(4d)及3-S-(2’,3’,4’,6’-O-四乙酰基-β-D-吡喃葡萄糖硫基)-4-N-(3,5-二溴邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑(5d)具有较强的抑菌活性.     

Synthesis and Anti-Inflammatory Properties of Substituted 5-(Tetrahydro-4-phenyl-2H-pyran-4-yl)-4H-1,2,4-triazole-3-thiols

Russian Journal of Organic Chemistry - 5-(Tetrahydro-4-phenyl-2H-pyran-4-yl)-4H-1,2,4-triazole-3-thiol was synthesized by the reaction of 4-phenyltetrahydropyran-4-carbonyl chloride with...     

Synthesis and pancreatic lipase inhibitory activities of some 1,2,4-triazol-5(3)-one derivatives

In this study, starting from 4-amino-5-(4-chlorobenzyl)-2,4-dihydro-3H-1,2,4-triazole-3-one ( 1 ), the 4-Amino-5-(4-chlorobenzyl)-2-undecyl-2,4-dihydro-3H-1,2,4-triazol-3-one ( 2 ) was first synthesized and this compound was converted to Schiff base derivatives ( 3a-e ). In the second step of the study, the 2-[3-(4-chlorobenzyl)-5-oxo-1-undecyl-1,5-dihydro-4H-1,2,4-triazole-4-yl]-acetohydrazide ( 6 ), which was used as a key product in the synthesis of many heterocyclic compounds was synthesized in four steps, and then this compound was converted into methylidene acetohydrazide ( 7a-e ), thiosemicarbazide ( 8a-e ), and 1,2,4-triazole-5-thione ( 9a-e ) derivatives. Also, in the last part of the study, 1,2,4-triazole-5-thione derivatives were changed into Mannich bases ( 10a-b ) bearing a 4-phenylpiperazine ring. These new compounds were tested with regard to pancreatic lipase (PL) inhibition activity, and compound 3b , 3d , 7d , 8d , and 9d showed a considerable anti-lipase activity at various concentrations. The activity of compounds 7b (IC₅₀ = 1.45 ± 0.12 μM) was the highest in terms of IC₅₀, comparable to that of orlistat, a well-known PL inhibitor used as an antiobesity drug.     

Crystal Structure and DFT Studies of a Triazole Derivative： 4- （ 2-Hydrobenzylideneamino ） -3- （ 1,2,4-triazol-4-ylmethyl） 1H-1, 2,4-triazole-5 （4H） -thione

A novel triazole derivative 4-(2-hydrobenzylideneamino)-3-(1,2,4-triazol-4-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione(1) was synthesized and characterized using elemental analysis, FTIR, and 1H NMR, and its crystal structure was determined via X-ray single crystal diffraction analysis. Crystal data: monoclinic, P2(1)/c, a=0.83335(9) nm, b=1.49777(16) nm, c=1.14724(12) nm, β =107.990(2)°, D=1.470 Mg/m3, and Z=4. The geometries and the vibrational frequencies were determined using the density functional theory(DFT) method at the B3LYP/ 6-31G level. To demonstrate the accuracy of the reaction route of compound 1, one of the important intermediates was also tested using the same method. The structural parameters of the two compounds calculated using the DFT study are close to those of the crystals, and the harmonic vibrations of the two compounds computed via the DFT method are in good agreement with those in the observed IR spectral data. The thermodynamic properties of the title compound were calculated, and the compound shows a good structural stability at normal temperature. The test results of biological activities show that it has a certain bactericidal ability.     

1H and 13C NMR study of 5-substituted-4- (arylidene)amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 6-aryl-3-(D-gluco- pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b] [1,3,4]thiadiazines

Five 5-substituted-4-(arylidene)amino-2,4-dihydro-3H-1, 2,4-triazole-3-thiones (2a-2e) and seven 6-aryl-3-(D-gluco-pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines (3a-3g) were synthesized. The complete 1H and 13C NMR chemical shift assignments were analyzed on one- and two-dimensional NMR techniques, including DEPT, NOE-DIF, COSY, gHMBC, and gHSQC.     

Synthesis, Crystal Structure and Biological Activities of N＇ - （ 4-Methoxybenzylidene ） -2- （ 1H-1, 2,4- triazol-1-yl） acetohydrazide

The title compound, N‘-( 4-methoxybenzylidene ) -2-( IH-1, 2,4-triazol-1-yl ) acetohydrazide, was synthesized and its structure was confirmed by means of IR, MS,^1H NMR and elemental analysis. The single crystal structure of the title compound was determined by X-ray diffraction. The preliminary biological test shows that the synthesized compound has a low antifungal activity.     

Synthesis of some new 4,5-substituted-4H-1,2,4-triazole-3-thiol derivatives

In this study appropriate hydrazide compounds, furan-2-carboxylic acid hydrazide (1) and phenylacetic acid hydrazide (2) were converted into 1,4-substituted thiosemicarbazides 4a-e and 5a-e and 4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7 and 10. The 1,4-substituted thiosemicarbazides were then converted into 5-(furan-2-yl or benzyl)-4-(aryl)-4H-1,2,4-triazole-3-thiols 8a-e and 9a-e. In addition, the azomethines 11a-d and 12a-d were prepared from the corresponding arylaldehydes and the 4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7 and 10. The structures of all the synthesized compounds were confirmed by elemental analyses, IR, (1)H-NMR and(13) C-NMR spectra.     

Synthesis and study of 3-(pyrimidin-2-yl)amino-1(2)H-1,2,4-triazole derivatives

The previously unknown 3-[4(3H)-pyrimidinon-2-yl]amino-1H-1,2,4-triazoles, which were converted to 3-[4-chloro-, 3-(4-ethoxy)-, 3-(4-hydrazinopyrimidin-2-yl)]-amino-2(4)H-1,2,4-triazoles, were obtained by the reaction of 2-nitroamino-4(3H)-pyrimidinones with 3-amino-5-hexyl-1H-1,2,4-triazole. The condensation of the initial products with -diketones gave 3-[4-(1H-pyrazol-1-yl)pyrimidin-2-yl]-amino-2(4)H-1,2,4-triazoles. The IR, UV, and PMR spectra of the synthesized compounds were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1678–1681, December, 1980.     

Synthesis of 3-(3-Alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl)aminocarbonylchromones

A series of 3-(3-alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl)aminocarbonylchromones has been prepared by oxidation of 3-formylchromone with Jones' reagent followed by reaction with 3-alkyl-4-amino-4,5-dihydro-1,2,4-triazole-5(1H)-thione in the presence of POCl³. The structures of the compounds were confirmed by IR, LC-MS, and ¹H NMR spectra and elemental analyses.     

A facile one-pot three-component synthesis of benzylideneamino-3,5-dimethyl-1H-pyrazoles

A facile, one-pot three-component protocol for the synthesis of substituted 4-(benzylideneamino)-5-(3,5-dimethyl-1H-pyrazol-1-yl)-4H-1,2,4-triazole-3-thiols have been reported by the reaction of 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol with acetyl acetone and various substituted benzaldehydes via multi component reaction. The newly synthesized derivatives were characterized by their elemental analysis and spectral data. The current strategy provides heterocyclic compounds in good yields with broad substrate scope.     

3-芳基-1-(吡啶-3-基)-2-(1H-1,2,4-三唑-1-基)-2-丙烯-1-醇的合成及生物活性研究

用硼氢化钠还原3-芳基-1-(吡啶-3-基)-2-(1H-1,2,4-三唑-1-基)丙烯酮, 合成了10个新型含吡啶基的三唑醇类化合物. 所有化合物均经核磁、元素分析确证. 生物活性测试结果表明, 部分化合物具有一定的杀菌活性及植物生长调节活性.     

1-[(6-烷(苄)氧基-3,4-亚甲二氧基)苯基]-2-(1H-1,2,4-三唑)-乙酮(醇)类化合物的合成及抑菌活性

为了寻找新的低毒高效杀菌剂,以芝麻酚和1-H-1,2,4-三唑为主要原料,合成了12个1-[6-烷(苄)氧基-3,4-二氧亚甲基）苯基] -2 -(1H-1,2,4-三唑)-乙酮(醇)类化合物。所有化合物的结构经IR, 1HNMR, 13C NMR确证。初步生物测试结果表明：在质量浓度为100μgmL下,化合物Ⅴc对小麦赤霉病菌的抑制率达到了81.3%;化合物Ⅳe对马铃薯干腐病菌的抑制率达到了83.4%;化合物Ⅴe,Ⅴf对玉米弯孢病菌的抑制率也分别达到了79.7%和72.4%;化合物Ⅳd对小麦赤霉病菌和马铃薯干腐病菌的抑制率分别达到了68.9%和65.7%。     

Synthesis, Crystal Structure, and Biological Activities of 2-Oxo-2-aryl-1 - （ 1,2,4-triazol-1 -yl ） ethyl phenylcarbamodithioate

IntroductionAs an important type of fungicide, compoundscontaining 1,2,4-triazole groups have attracted muchattention because they exhibit a certain fungicidal acti-vity againstPuccinia reconditeand also play a role inroot-growth regulation[1—3]. However…