Synthesis and biological activities of new 1H‐1,2,4‐triazole alcohol derivatives containing a ferrocenyl moiety

Fourteen new 1H‐1,2,4‐triazole alcohol derivatives containing a ferrocenyl moiety were synthesized. In addition, six unexpected compounds, the hydroxyls of the title compounds, methylated by methanol, were obtained. The structures of all these new compounds were confirmed using ¹H NMR spectra, ¹³C NMR, MS and elemental analyses. Some compounds were also confirmed with IR spectra. The antifungal and plant growth regulatory activities of the title compounds are discussed. Copyright © 2008 John Wiley & Sons, Ltd.     

Synthesis,structures, and biological activities of new 1H‐1,2,4‐triazole derivatives containing pyridine unit

Fourteen new 1H‐1,2,4‐triazole derivatives containing pyridine moiety were synthesized by condensation of 1‐(pyridine‐3‐yl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)ethanone with aryl aldehydes, and their reaction conditions were studied. The title compounds were screened for their antibacterial and plant growth regulatory activities. The screening data revealed that most of the compounds showed some antifungal and plant growth regulatory activities. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:376–380, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20308     

3-氨基-1H-1,2,4三唑类席夫碱的合成和生物活性

以醋酸为催化剂,用3-氨基-1H-1, 2, 4-三唑与取代苯甲醛反应合成了8个3-氨基-1H-1, 2, 4-三唑类席夫碱,化合物结构经1H NMR,IR和元素分析证实,并对其进行了生物活性测试,初步生物活性结果表明此类化合物具有良好的杀菌活性。     

Proton conducting polymers containing 1H‐1,2,3‐triazole moieties

Polyacrylates containing a different number of 1H‐1,2,3‐triazole groups per repeat unit have been synthesized via conventional free radical polymerization. These polymers were characterized by nuclear magnetic resonance spectroscopy (NMR), gel permeation chromatography (GPC), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). Proton conductivity measurements were made using impedance spectroscopy. Introduction of more than one triazole per repeat unit did not result in an increase in conductivity as there was an accompanying increase in glass transition temperature (T_g). A maximum conductivity of 17.5 μS/cm was obtained at 200 °C under anhydrous condition. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 188–196, 2009     

Synthesis of chiral fused heterocyclic compounds containing 1,2,4‐triazole ring

A series of new chiral (S)‐3‐ary1‐6‐pyrrolidin‐2‐yl‐[1,2,4]triazolo[3,4‐b]thiadiazole (II_1‐5), (S)‐1‐(3‐aryl‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazol‐6‐yl)‐ethylamine (II_6‐8) and (S)‐1,2‐bis(3‐aryl‐[1,2,4]triazolo‐[3,4‐b][1,3,4]thiadiazol‐6‐yl)‐ethylamine (II_9‐11) were prepared by the condensation of 3‐aryl‐4‐amino‐5‐mercapto‐1,2,4‐triazoles with different L‐amino acids in the presence of phosphorus oxychloride and evaluated for their antibacterial activity.     

Synthesis of novel 1,3‐substituted 1H‐[1,2,4]‐triazole‐3‐thiol derivatives

By means of regioselective S‐alkylation of 1H‐1,2,4‐triazole‐3‐thiol ( 1 ), a series of S‐substituted derivatives 2a‐j were synthesized. In certain conditions, the reaction of 2 with arylsulfochlorides, arylisocyanates, and quaternary ammonium salts of azines corresponding compounds were obtained 1‐arylsulfonyl‐ (3a‐d) , 1‐arylcarbonamido‐ ( 4a,b ), and 1‐azinyl‐1,2,4‐ ( 6a‐p ) triazoles. Structures of compounds were confirmed by ¹H NMR and elemental analyses. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 20:405–410, 2009; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20565     

Synthesis of 1,3‐thiazole and 1,2,4‐oxadiazole substituted spiro[3H‐indole‐3,2′‐thiazolidine]‐2,4′(1H)‐diones

Some new derivatives of spiro[3H‐indole‐3,2′‐thiazolidine]‐2,4′(1H)‐dione with the heterocyclic ring such as substituted thiazole and 1,2,4‐oxadiazole attached to the indolinone ring via CH₂ linkage has been synthesized in moderate yields. The synthesis have been carried out by making use of the reactivity of the NH group of the indolinone moiety present in spiro[3H‐indole‐3,2′‐thiazolidine]‐2,4′(1H)‐dione.     

Copper(II) Halide Complexes with 1‐tert‐Butyl‐1H‐1,2,4‐triazole and 1‐tert‐Butyl‐1H‐tetrazole

1‐tert‐Butyl‐1H‐1,2,4‐triazole (tbtr) was found to react with copper(II) chloride or bromide to give the complexes [Cu(tbtr)₂X₂]_n and [Cu(tbtr)₄X₂] (X = Cl, Br). 1‐tert‐Butyl‐1H‐tetrazole (tbtt) reacts with copper(II) bromide resulting in the formation of the complex [Cu₃(tbtt)₆Br₆]. The obtained crystalline complexes as well as free ligand tbtr were characterized by elemental analysis, IR spectroscopy, thermal and X‐ray analyses. For free ligand tbtr, ¹H NMR and ¹³C NMR spectra were also recorded. In all the complexes, tbtr and tbtt act as monodentate ligands coordinated by Cu^II cations via the heteroring N⁴ atoms. The triazole complexes [Cu(tbtr)₂Cl₂]_n and [Cu(tbtr)₂Br₂]_n are isotypic, being 1D coordination polymers, formed at the expense of single halide bridges between neighboring copper(II) cations. The isotypic complexes [Cu(tbtr)₄Cl₂] and [Cu(tbtr)₄Br₂] reveal mononuclear centrosymmetric structure, with octahedral coordination of Cu^II cations. The tetrazole compound [Cu₃(tbtt)₆Br₆] is a linear trinuclear complex, in which neighboring copper(II) cations are linked by single bromide bridges.     

Synthesis and antimicrobial and pharmacological properties of new thiosemicarbazide and 1,2,4‐triazole derivatives

Reaction of 4‐phenyl‐4H‐1,2,4‐triazole‐3‐thione with ethyl bromoacetate has led to the formation of ethyl [(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)sulfanyl]acetate 1 , the structure of which was confirmed by X‐ray analysis. In the next reaction with 80% hydrazide hydrate, appropriate hydrazide 2 was obtained, which in reaction with isothiocyanates was converted to new acyl derivatives of thiosemicarbazides 2 , 3 , 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h . The cyclization of these compounds in alkaline media has led to formation of new derivatives of 5‐{[(4‐phenyl‐4H‐1,2,4‐triazole‐3‐yl)sulfanyl]methyl}‐4H‐1,2,4‐triazole‐3(2H)‐thiones 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4j . The structure of the compounds was confirmed by elementary analysis and IR, ¹H‐NMR, ¹³C‐NMR, and MS spectra. Compounds 2 , 3 , 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h and 4a , 4b , 4c , 4d , 4e , 4f , 4g were screened for their antimicrobial activities, and the influence of the compounds 4a , 4b , and 4e , 4f , 4g on the central nervous system of mice in behavioral tests was examined. J. Heterocyclic Chem., (2011).     

Synthesis of some trifluoromethyl substituted 1‐methylpyrazoles

The major products from the reaction of β‐alkoxyvinyl trifluoromethyl ketones 1a‐c with methylhydrazine ( 2 ) in absolute ethanol are the 3‐(trifluoromethyl)‐substituted‐1‐methylpyrazoles 3a‐3c with lesser amounts of the 5‐(trifluoromethyl)‐substituted products 4a‐4c and 5a‐5c. Carrying out the reaction in non‐polar, aprotic solvents can further enhance the regioselectivity favoring the 3‐ (trifluoromethyl) ‐substituted isomers.     

Convenient synthesis of some new substituted pyrazolyl‐1,3,4‐oxadiazoles and pyrazolyl‐1,2,4‐triazoles

A simple and versatile method for the synthesis of pyrazol‐3‐yl‐1,3,4‐oxadiazole, pyrazol‐3‐yl‐1,2,4‐triazole, (1,5‐diphenylpyrazol‐3‐yl)‐(3,5‐dimethyl‐1‐carbonyl)pyrazole and (1,5‐diphenylpyrazol‐3‐yl)‐(5‐hydroxy‐3‐metheyl‐1‐carbonyl)pyrazole derivatives from 1,5‐diphenylpyrazole‐3‐carboxylic acid hydrazide has been developed.     

Design and synthesis of diheterocyclic compounds containing tetrazolinone and 1,2,4‐triazole

A novel series of 1‐(4‐chlorophenyl)‐4‐{[5‐(alkylthio)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl]methyl}‐1,4‐dihydro‐5H‐tetrazol‐5‐ones 6a‐y were synthesized in good to excellent yields and their structures were identified by ¹H nmr, ¹³C nmr, ms and elemental analysis. Determining the X‐ray crystallography of compound 6j indicated that there were strong intermolecular hydrogen bonds in the stacking interactions. The bioassay results showed that compound 6k exhibited good insecticidal activities against T cinnabarinus at the dosage of 250 mg.L^?1. To our knowledge, this is the first report about the insecticidal activity of tetrazolinone derivatives.     

Synthesis of some 3‐aryl‐1H‐isochromene‐1‐thiones

A rapid microwave‐accelerated thionation of some 3‐substitued isocoumarins to corresponding 1‐thio‐isocoumarins was achieved employing Lawesson's reagent under solventless conditions.     

Synthesis of some new 1H‐benzimidazole‐2‐carboxamido derivatives and their antimicrobial activitiy

5,6‐Dichloro‐2‐hydroxymethyl‐1H‐benzimidazole ( 1 ) was prepared by the cyclization of 4,5‐dichloro‐o‐phenylenediamine with glycolic acid, then, alcohol group of 1 was converted to carboxylic acid ( 2 ). The final products 5,6‐dichloro‐1H‐benzimidazole‐2‐carboxamides ( 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 13 , 14 ) were prepared by the amidification of compounds 2 with several amines by using O‐(benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium hexafluorophosphate. Compound 12 was prepared by the reaction of compound 6 with methanolic HCl. The relations between the tautomer and nontautomer types of imidazole moiety are discussed with NMR spectroscopy. The in vitro antibacterial and antifungal activity of the synthesized compounds against S. aureus, E. coli, B. subtilis, and C. albicans were evaluated with the disc diffusion techniques. The synthesized compounds were more active against the bacteria than fungi. Compound 3 exhibited best inhibitory activity against S. aureus. J. Heterocyclic Chem., (2011).     

Three 1,2,4‐triazole derivatives containing subtituted benzyl and benzyl­amino groups

The title compounds, 4‐benzyl­amino‐3‐(4‐methyl­benzyl)‐1H‐1,2,4‐triazol‐5(4H)‐one, C₁₇H₁₈N₄O, (I), 3‐(4‐methyl­benzyl)‐4‐(4‐methyl­benzyl­amino)‐1H‐1,2,4‐tri­azol‐5(4H)‐one, C₁₈H₂₀N₄O, (II), and 3‐(4‐chloro­benzyl)‐4‐(4‐methyl­benzyl­amino)‐1H‐1,2,4‐triazol‐5(4H)‐one, C₁₇H₁₇ClN₄O, (III), were obtained from the corresponding Schiff base in the presence of diglyme and NaBH₄. Each compound contains a 1,2,4‐triazole ring and two benzene rings, which are essentially planar. The molecules are linked by a combination of intermolecular N—H⋯O and N—H⋯N hydrogen bonds. Additionally, there is a weak π–π stacking interaction in (I), involving the benzene ring of the amino­benzyl group and the partially aromatic 1,2,4‐triazole moiety, with a centroid–centroid distance of 3.7397 (10) Å.     

Synthesis of 1‐nonanoyl/octadecanoyl‐4‐substituted thiosemicarbazides and substituted 1,2,4‐trizoles as biological active compounds

4‐Alkyl/aryl‐5‐nonanoyl/octadecanoyl‐2,4‐dihydro‐3H‐1,2,4‐triazoline‐3‐thiones were synthesized as potential antimicrobial agents. The course of synthesis included the reaction of nonanoyl/octadecanoyl hydrazines with selected alkyl/aryl isothiocyanates. The prepared thiosemicarbazides gave by cyclization the required 1,2,4‐triazoles. A number of synthesized compounds were subjected to in vitro testing against two gram‐positive, two gram‐negative bacteria and two fungi.