Rearrangement of enol acetates of α-(3,5-dimethyl-1,2,4-triazol-1-yl)-2,4-dichloroacetophenone and α-(1,2,4-triazol-1-yl)-2,4-dichloropropiophenone

At 140 °C in acetic anhydride enol acetates of -(3,5-dimethyl-1,2,4-triazol-1-yl)-2,4dichloroacetophenone and -(1,2,4-triazol-1-yl)-2,4-dichloropropiophenone undergo 1,3and 1,5-rearrangement, respectively.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 182–184, January, 1995.     

Nitrosation of 4-amino-1-phenacyl-1,2,4-triazolium bromides and ω-(1,2,4-triazol-1-yl)acetophenones

The reaction of 4-amino-1-phenacyl-1,2,4-triazolium bromides with an excess of nitrous acid leads to a mixture of the corresponding -(1,2,4-triazol-1-yl)-acetophenones and -hydroximino--(1,2,4-triazol-1-yl)acetophenones. Products of the latter type are formed during nitrosation at the methylene group of both the intermediate -triazolylacetophenones, and the starting 4-amino-1-phenacyl-1, 2,4-triazolium bromides. The role of Br^– as a catalyst is significant for both nitrosation paths. In the reaction of -(1,2,4-triazol-1-yl)acetophenones with HNO₂, SCN^– is a more active catalyst than Br^–. During the nitrosation of para-substituted 4-amino-1-phenacyl-1,2,4-triazolium bromides, the yield of -hydroximino--(1,2,4-triazol-1-y1)acetophenones increases with increase in the acceptor properties of the aryl substituent, which is explained by the increase in the CH-acidity of the nitrosation substrates.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2821–2824, December, 1991.     

Synthesis,Structure and Biological Activities of 2-(1H- 1,2,3-Benzotriazol-1-yl)-1-(4-methylphenyl)-2- (1H-1,2,4-triazol-1-yl)-1-ethanone

IntroductionTriazole derivatives have become the most rapidlyexpanding group of antifungal compounds with advanta-ges of lowtoxicity, high oral bioavailability and broad-spectrum antifungal activity, which can be used againstfungi including most yeasts an…     

Synthesis and Biological Activities of ω-Heterocyclyl-ω-(1H-1,2,4-triazol-1-yl) Acetophenones

Inrecentyears,agreatvarietyofheterocycliccompoundsbearing1H-l,2,4-triazoleringhavebeensynthesizedduetotheirbroadspectrumbiologicalactivitiesincludingantiinflammatory.insecticidal,antiviralandantiturnoractivities'-',someofwhichhavebeendevelopedintocommerciallyantifungalagentssuchastriadimefon.triadimenolanddiniconazele.Wepreviouslysynthesizedmanykindsofheterocycliccompoundssuchasl,3,4-oxadiazole,l,2,4-triazole,l,3.4-thiadiazoleandl,2.3-triazolederivativeswhichexhibitedantibacterial,antitubercul…     

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

IntroductionBoth triazole derivatives and Schiff base are repor-ted to possess significant antifungal and plant-growthregulatory activities[1—6].Further,triazole drugs are al-so very common in the medical field.These give a greatimpetus to the research for potential pharmacologicallyactive Schiff base containing triazole.In order to search for newtriazole compounds withhigher biological activity,the title compound was syn-thesized and its biological activities were tested.Also,its structure…     

Synthesis of 1-(3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranosyl)uracils via an α,β-unsaturated aldehydrohexose

Summary Mercuric catalyzed hydrolysis of acetylatedL-rhamnal1 gave the ,-unsaturated aldehyde2. 1,2,4-Triazole was coupled, in a Michael type addition reaction, to2 at C-3 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to give, after acetylation at the anomeric center, an anomeric mixture of 1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose (3). Reaction of3 with silylated 2,4-dihydroxypyrimidines4 in the presence of trimethylsilyl triflate as catalyst followed by deprotection with 33% methylamine in absolute ethanol afforded the corresponding nucleosides7 and8.

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Synthese von 1-(3-(1,2,4-Triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranosyl)uracilen über eine ,-ungesättigte Aldohexose

Zusammenfassung Die quecksilberkatalysierte Hydrolyse von acetyliertemL-Rhamnal1 ergab die ,-ungesättigten Aldehyde2. 1,2,3-Triazol wurde in Gegenwart von 1,8-Diazabicyclo[5.4.0]-7-undecen mittels einer Addition vom Michael-Typ an C-3 von2 gekoppelt und ergab dann nach Acetylierung am anomeren Zentrum eine anomere Mischung von 1,5-Di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose (3). Die Reaktion von3 mit silyliertem 2,4-Di-hydroxypyrimidinen4 in Gegenwart von Trimethylsilyltriflat in absolutem Ethanol ergab die entsprechenden Nucleoside7 und8.

     

Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives

Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl₃ and P₂O₅ Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4,9-dihydro-3H-β-carbolines that can be transformed into β-carboline and tetrahydro-β-carboline derivatives.     

Syntheses,crystal structures,and fluorescence of two complexes constructed by N ′-(pyridin-2-ylmethylene)-2-( 1H -1,2,4-triazol-1-yl)acetohydrazide

Two new binuclear complexes, Cd₂(HL)₂(NO₃)₄?·?(CH₃OH)₂ (1) and Cu₂(L)₂(ClO₄)₂ (2), based on N′-(pyridin-2-ylmethylene)-2-(1H-1,2,4-triazol-1-yl)acetohydrazide (HL) and Cd(II) and Cu(II) salts have been synthesized and characterized by single crystal X-ray diffraction. Hydrogen bonds and π–π interactions extend both binuclear molecules, a 3-D supramolecular framework for 1 and 1-D staggered chains for 2. Fluorescence of both complexes is discussed.     

Structure and Biological Activities of 2-（ 1,3-Dithiolan-2-ylidene）-1-phenyl-2- （ 1,2,4-triazol-1 -yl ） ethanone

In order to find leading compounds with an excellent fungicidal activity, the title compound 2-（ 1,3-dithiolan-2- yl-idene）-1-phenyl-2-（ 1,2,4-tfiazol-1-yl） ethanone was synthesized according to the biological isosterism and its structure was confirmed by means of IR, MS, ^1 H 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 exhibits some biological activities.     

Synthesis and Antibacterial Activities of 4-Amino-3-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-5-mercapto-1,2,4-triazoles/2-Amino-5-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-1,3,4-thiadiazoles and Their Derivatives

ＩｎｔｒｏｄｕｃｔｉｏｎＳｃｈｉｆｆｂａｓｅｓ ,ａｍｉｄｅｓ ,ｉｍｉｄａｚｏｌｏ[2 ,1 ｂ] 1,3,4 ｔｈｉａｄｉａｚｏｌｅｓ,ａｎｄ 7Ｈ ｓ ｔｒｉａｚｏｌｏ[3,4 ｂ] 1,3,4 ｔｈｉａｄｉ ａｚｉｎｅｓｃｏｎｔａｉｎｉｎｇｈｅｔｅｒｏｃｙｃｌｅｓｈａｖｅｂｅｅｎａｔｔｒａｃｔｉｎｇｍｕｃｈａｔｔｅｎｔｉｏｎａｓｐｏｔｅｎｔｉａｌａｎｔｉｆｕｎｇａｌａｇｅｎｔｓ .1 51,2 ,3 ｔｒｉａ ｚｏｌｅ ,6 7ｍｅｒｃａｐｔｏ 1,2 ,4 ｔｒｉａｚｏｌｅ ,81,3,4 ｔｈｉａｄｉａｚｏｌｅ9 10ａｎｄｔｈｅｉｒｒｅｌａｔｅｄｃｏ…     

Structure and Biological Activities of 3-Phenyl-2-[1-benzoyl-1- （1,2,4-triazol-1-yl）] Methenyl Thiazolidine

The title compound 3-phenyl-2-[1-benzoyl-1-(1,2,4-triazol-1-yl)]methenyl thiazolidine was synthesizedfrom acetophenone, triazole, phenylthioisocyanate and 1,2-dibromo-ethane by several step reactions. Itsstructure was identified by means of ^1H NMR, MS and IR spectrometries. The single crystal structure of 3-phenyl-2-[1-benzoyl-1-(1,2,4-triazol-1-yl)]methenyl thiazolidine was determined by X-ray diffraction.The preliminary bioassays have shown that the title compound exhibits the weak activities of fungicide andplant growth regulator.     

Cationic Cd(II) metal − organic framework based on tetrakis(1,2,4-triazol-1-yl)methane

Abstract

Solvothermal reaction of a multidentate ligand (tetrakis[4-(1-triazolyl)phenyl]-methane (ttpm)), with Cd(NO₃)₂ afforded a cationic Cd(II) coordination polymer {[Cd(ttpm)·DMSO]·2NO₃}_n. Single-crystal X-ray diffraction analyses showed that ttpm belonged to the tetragonal space group I4₁/a, and 1 was a 2-D (4,4) network. 1-D channels along the c direction exist in the 3D stacking map to accommodate the charge-balancing NO₃^? anions. N₂ adsorption/desorption experiments showed the framework had a BET surface area of 11.36?m²·g^?1. Compared with luminescence of ttpm, 1 showed red-shifted luminescence spectra with higher intensity from the more rigid arrangement of the π systems.     

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…     

Synthesis, Structure and Biological Activities of 2- （4-Met hoxybenzoyl ）-N-phenyl- 2- （ 1,2,4-triazol- 1-yl ） thioacetamide

The title compound, 2-(methoxybenzoyl)-N-phenyl-2-(1,2,4-triazol-l-yl) thioacetamide was synthesized by several reactions from 4-methoxyacetophenone, triazole and phenyl isothiocyanate. The structure was identified by elemental analysis, ^1H NMR, MS and IR. The single crystal structure of 2-(methoxybenzoyl)-N-phenyl-2-(1,2,4-triazol-l-yl)thioacetamide was determined withX-ray diffraction. The preliminary bioassays show that the title compound exhibits weak antifungal activities and plant-growth regulatory activity.     

Synthesis and Crystal Structure of N′-(4-fluorobenzylidene)-2-(1H-1,2,4-triazole-1-yl)acetohydrazide

IntroductionBoth triazole derivatives and Schiff base have beenreported to possess significant antifungal[1—3]and plantgrowth regulatory activities[4—6].Triazole drugs are alsovery common in the medical field,which has given animmense impetus to the res…     

Synthesis,Crystal Structure and Fungicidal Activity of N-（4-tert-buty）-5-（1,2,4-triazol- 1-yl）thiazol-2-yl）propionamide

The title compound has been synthesized by the reaction of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-aminothiazole with propionic anhydride, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group Pbca with a = 18.441(2), b = 8.3284(9), c = 19.257(2) , Z = 8, V = 2957.5(5) 3, Mr = 279.37, Dc = 1.255 mg/m3, S = 1.033, μ = 0.219 mm-1, F(000) = 1184, the final R = 0.0349 and wR = 0.0876 for 2629 observed reflections(I 2σ(I)). X-ray crystal structure presents the intermolecular N–H···N hydrogen bond, which plays an important role in stabilizing the crystal structure. The preliminary bioassay indicates that the title compound exhibits potent fungicidal activity against R. Solani(25 mg/L) with inhibition rate of 80.0%.     

Syntheses,Structure and Biological Activities of 2-(1H-Benzo [1,2,3]triazole-1-yl)-1-(3-methyl-4-bromobiphenyl)-2-(1H-1,2,4-triazole-1-yl)ethanone

Introduction1,2,4-Triazole derivatives represent an interesting class of heterocyclic compounds[1]and have become the most rapidly expanding group of antifungal compounds with the advantages of toxicity, high oral bioavailabi-lity, and broad spectrum of a…     

Synthesis and study of N-(1-phenylethylidene)-N-(4H-1,2,4-triazol-4-yl)amine, N′-(4H-1,2,4-triazol-4-yl)benzamidine, and cobalt(ii), nickel(ii), and copper(ii) complexes based on these ligands

Methods were developed for the synthesis of complexes of Co^II, Ni^II, and Cu^II nitrates and chlorides with N-(1-phenylethylidene)-N-(4H-1,2,4-triazol-4-yl)amine (L¹) and N′-(4H-1,2,4-triazol-4-yl)benzamidine (L²). The Co^II and Ni^II complexes have a linear trinuclear structure. The Cu^II complexes are polynuclear. Both ligands are coordinated to the metal ions in a bidentate-bridging mode through the N(1) and N(2) atoms of the heterocycle. In all compounds, the coordination polyhedron can be described as a distorted octahedron. The molecular and crystal structure of the [Ni₃(L¹)₆(EtOH)₂(H₂O)₄](NO₃)₆·2EtOH·4H₂O complex was established.     

Thermal Behavior and Decomposition Kinetics of the Complexes of CuX_2 (X=NO_3, Br, Cl and ClO_4) with 3,3''''-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

Introduction N-1-Alkyl-substituted 1,2,4-triazole compounds, like some other heterocyclic derivatives containing nitrogen, have recently been the subjects of numerous studies due to their fungicidal action1 and plant growth regulation.2 Among them, the complexes with a sort of triazole as ligand are of considerable interest because of their broad-spectrum bioactivity, coordination and photo-chemical properties, as well as many potential applica-tions in various fields.3,4 In our previous paper…