5-Amino-3-nitro-1,2,4-triazole and Its Derivatives

The review summarizes published data on the structure, tautomeric properties, direct, indirectmethods of preparation, chemical properties, and reactivity of 5-amino-3-nitro-1,2,4-triazole which is one of the most important synthons of the symmetric triazole series.     

Effect of 3-Amino-5-mercapto-1,2,4-triazole on Electroless Nickel Deposition

The effects of organic additive, 3-amino-5-mercapto-1,2,4-triazole （AMTA） on bath stability, deposition rate, reaction activation energy, and Ni-P coating composition in acidic electroless nickel plating were investigated. Polarization curve method and infrared reflection spectroscopy were used to analyze the mechanism of the effect of AMTA on electroless nickel deposition. It was observed that AMTA improved bath stability, decreased the deposition rate, and increased the reaction activation energy. It was also revealed that AMTA decreased the phosphorus content and increased the sulfur content in Ni-P coating. In addition, AMTA inhibited the anodic oxidation of hypophosphite and accelerated the cathodic reduction of Ni^2＋. Infrared reflection spectroscopy result indicates that AMTA was adsorbed on the surface of Ni-P and interacted with Ni^2＋ to form an AMTA-Ni^2＋ compound. On the basis of the results of this study, the mechanism of the effect of AMTA on electroless nickel deposition was deduced.     

5-苄基-4-氨基-3-巯基-1,2,4-三唑席夫碱合成与生物活性研究

为进一步研究三唑席夫碱化合物的合成与性质,以熔融法合成中间体5-苄基-4-氨基-3-巯基-1,2,4-三唑,再与取代醛在冰醋酸催化下回流反应合成了6个1,2,4-三唑席夫碱化合物,其结构通过元素分析,红外光谱,核磁共振氢谱进行了表征。生物测试结果表明,合成的三唑席夫碱化合物对烟草赤星病、马铃薯干腐病、小麦赤霉病、番茄早疫病、西瓜枯萎病5种植物病原菌具有较好的抑菌活性。     

Condensed systems based on 4-amino-3-mercapto-1,2,4-triazole

1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazines, hydrazones, and -thio adducts were obtained by reactions of 4-amino-3-mercapto-1,2,4-triazole with -bromoacetophenones, aldehydes, and ,-unsaturated ketones. Conditions that promote the cyclocondensation of the -thio adducts to the previously undescribed 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazepines were found. The chemical and spectral properties of the compounds obtained are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 267–272, February, 1992.     

Iodocyclization of S-allyl derivatives of 3-mercapto-4-methyl-1,2,4-triazole

It has been established that iodocyclization of 3-(2-methyl-2-propenyl)thio-4-methyl-1,2,4-triazole occurs regioselectively with annelation of the thiazole ring, 3-(3-methyl-2-butenyl)thio-4-methyl-1,2,4-thiazole with annelation of the thiazine ring, and 3-allylthio-4-methyl-1,2,4-triazole with annelation of both rings to form derivatives of [1,3]thiazolo[3,2-b][1,2,4]triazolium and [1,2,4]triazole[5,1-b][1,3]thiazinium iodides.     

Reactions of 3-azido-1,2,4-triazole with electrophiles

Alkylation of 3-azido-1,2,4-triazole with oxiranes, bromoacetone, and methyl vinyl ketone furnished a mixture of N-substituted 3- and 5-azido-1,2,4-triazoles, 3-azido compounds prevailing. The same substrate subjected to heterylation with 3,5-dinitro-1,2,4-triazole derivatives reacted selectively at the N¹ atom, and its bromination afforded 3-azido-5-bromo-1,2,4-triazole..Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 11, 2004, pp. 1699–1704.Original Russian Text Copyright © 2004 by Kofman, Krasnov.     

FT Raman and FT-IR spectral studies of 3-mercapto-1,2,4-triazole

The FT-IR and FT Raman spectra of 3-mercapto-1,2,4-triazole have been recorded. The observed frequencies were assigned to various modes of vibrations on the basis of normal coordinate calculations, assuming Cs point group symmetry. The potential energy distribution associated with normal modes is also reported here. The assignment of fundamental vibrations agrees well with the calculated frequencies.     

4-Amino-3-methyl-5-mercapto-1,2,4-triazole as a gravimetric reagent for determination of silver in silver compounds, alloys and complexes

A simple, convenient and accurate gravimetric method for the determination of silver is presented. 4-Amino-3-methyl-5-mercapto-1,2,4-triazole precipitates silver quantitatively from ammoniacal tartrate medium. The complex is weighed as AgC(3)H(5)N(4)S after drying at 120-30 degrees . Separation of silver from a large number of cations is described. Application of the method for quantitative analysis of alloys and complexes of silver is reported. The average relative error for the range 20-70 mg of silver is +/- 0.25% and the relative standard deviation at the 40-mg level is 0.2%.     

Alkylation of 5-Amino-1,2,4-triazole with 1,2-Dibromoethane

Russian Journal of General Chemistry -     

3-芳基-5-巯基-1,2,4-三唑的亲核取代反应研究

以3-芳基-5-巯基-1,2,4-三唑为原料合成了20个3-芳基-1,2,4-三唑-5-巯基乙酸乙酯(2a～e)、3-芳基-1,2,4-三唑-5-巯基乙酸(3a～e)、3-芳基-5,6-二氢噻唑并[2,3-c]均三唑(5a～e)和3-芳基-6,7-二氢均三唑并[3,4-b][1,3]噻嗪(6a～e)。研究了3a～e在微波辐射下的环化反应，合成了5个3-芳基-5-氧代-6H-噻唑[2,3-c]均三唑(4a～e)。产物经元素分析、红外、核磁共振以及质谱方法确定了结构。初步研究了代表化合物的生物活性。     

Synthesis of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazepines and 4-amino-3-acylvinylthio-1,2,4-triazoles by reaction o acylacetylenes with 4-amino-3-mercapto-1,2,4-triazole

1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazepines have been prepared by treating -acetylenic ketones with 4-amino-3-mercapto-1,2,4-triazole in glacial acetic acid. Terminal acetylenic ketones react with the triazole to form 4-amino-3-acylvinylthio-1,2,4-triazoles. Heating the latter with hydrazine hydrate in alcohol yields substituted pyrazoles.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 990–994, July, 1991.     

Study on the Intramolecular Mannich Reaction of 4-Amino-3-aryl-2,3-dihydrogen-5-mercapto-1,2,4-triazoles

Seventeen novel fused heterocycles have been prepared by the intramolecular Mannich reaction of 4-amino-3-aryl-5-mercapto-1,2,4-triazole with aldehydes in the presence of acid, Yield: 32 ～ 90%. These compounds were screened for their antimicrobial activities.     

A Coupling Reaction of 4-Amino-5-mercapto- 3-substituted-1,2,4-triazoles to Generate Symmetrically Substituted Hydrazines

Summary. A novel coupling reaction of 4-amino-5-mercapto-3-substituted-1,2,4-triazoles to generate symmetrically substituted hydrazines, N,N′-bis(5-mercapto-3-substituted-1,2,4-triazol-4-yl)hydrazines was unexpectedly observed. Five examples are presented to demonstrate this reaction. All isolated products were unambiguously characterized.     

3-氨基-1,2,4-三氮唑自组装膜对黄铜的缓蚀作用

3-氨基-1,2,4-三氮唑(ATA)是一种环境友好型金属处理剂, 以其在黄铜表面制备了自组装单分子膜(SAMs), 用电化学方法研究ATA SAMs对黄铜的缓蚀作用及其吸附行为. 结果表明, ATA分子易在黄铜表面形成稳定的ATA SAMs, SAMs抑制了黄铜的阳极氧化过程, 改变了电极表面的双电层结构, 固/液界面双电层电容明显降低, 有良好的缓蚀效果. 研究结果还表明, ATA的吸附行为符合Langmuir吸附等温式, 吸附机理是典型的化学吸附.     

微波促进下3-(2-苯并呋喃基)-4-氨基-5-巯基-1,2,4-三唑

微波辐射条件下, 首先由2-苯并呋喃甲酰肼依次与二硫化碳和水合肼反应合成3-(2-苯并呋喃基)-4-氨基-5-巯基- 1,2,4-三唑, 进一步在微波辐射条件下由4-氨基-5-巯基-1,2,4-三唑分别与芳甲酸/芳氧基乙酸、α-溴代苯乙酮及芳醛反应以较高产率制得了相应的1,2,4-三唑并[3,4-b]-1,3,4-噻二唑、1,2,4-三唑并[3,4-b]-1,3,4-噻二嗪及4-芳亚甲基亚胺基-5-巯基-1,2,4-三唑. 产物结构经IR, ¹H NMR, MS及元素分析进行了表征.     

4-氨基-1,2,4-三唑苦味酸盐的晶体结构、比热容和热力学性质

利用4-氨基-1,2,4-三唑与苦味酸的甲醇溶液制备了4-氨基-1,2,4-三唑苦味酸盐,并于室温下培养出单晶。通过X射线单晶结构分析法测定其晶体结构,晶体属于正交晶系,空间群为Pbcn,晶胞参数为:a=0.9207(3)nm,b=1.9874(6)nm,c=1.3304(4)nm,β=90°,V=2.434(5)nm3,Dc=1.709g/cm3,Z=8,F(000)=1280,R1=0.0584,wR2=0.1840。运用DSC测得配合物在298.15K时的标准摩尔比热容为484.39J/(mol.K),比热容与温度的关系式为:Cp(J/(g.K))=0.4435+3.6997×10-3T。