- TBHP/TBAI–Mediated simple and efficient synthesis of 3,5-disubstituted and 1,3,5-trisubstituted 1H-1,2,4-triazoles via oxidative decarbonylation of aromatic aldehydes and testing for antibacterial activities
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The author has developed a simple, efficient and eco–friendly convenient general method for synthesis of 3,5–disubstituted–1,2,4–triazoles and 1,3,5–trisubstituted–1,2,4–triazoles from 3–monosubstituted–1,2,4–triazoles and 1,3–disubstituted–1,2,4–triazoles respectively using tetrabutylammonium iodide (TBAI) as catalyst and TBHP as oxidant under mid reaction conditions. This method provides structurally diverse 3,5–disubstituted 1,2,4–triazoes and 1,3,5––trisubstituted–1,2,4–triazoles in good to excellent yields. 3,5–Disubstituted 1,2,4–triazoes and 1,3,5––trisubstituted–1,2,4–triazoles derivatives are biologically and pharmaceutically active molecules, and therefore, this protocol could be of wide applications in medicinal chemistry and organic chemistry.
- Agisho, Habtamu Abebe,Esatu, Habdolo,Hairat, Suboot,Zaki, Mehvash
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supporting information
(2020/05/19)
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- Heterogeneous Copper(I)-Catalyzed Cascade Addition-Oxidative Cyclization of Nitriles with 2-Aminopyridines or Amidines: Efficient and Practical Synthesis of 1,2,4-Triazoles
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The heterogeneous cascade addition-oxidative cyclization of nitriles with 2-aminopyridines or amidines was achieved in 1,2-dichlorobenzene or DMSO at 120-130 °C by using a 1,10-phenanthroline-functionalized MCM-41-supported copper(I) complex [Phen-MCM-41-
- Xia, Jianhui,Huang, Xue,Cai, Mingzhong
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p. 2014 - 2022
(2019/04/26)
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- An efficient and recyclable heterogeneous catalytic system for the synthesis of 1,2,4-triazoles using air as the oxidant
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Copper-zinc supported on Al2O3-TiO2 was found as a simple and efficient heterogeneous catalyst for the oxidative synthesis of 1,2,4-triazole derivatives using air as the green oxidant under ligand-, base- and additive-free conditions. The heterogeneous reactions carried out smoothly with a large range of substrates, including NO2-, vinyl-, pyrimidine- and imidazole-contained starting materials, and provided corresponding triazoles in moderate to excellent yields with low catalyst loading (1.6 mol%). Furthermore, the catalyst can be simply recycled many times without significant loss in catalytic activity. The Royal Society of Chemistry.
- Meng, Xu,Yu, Chaoying,Zhao, Peiqing
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p. 8612 - 8616
(2014/03/21)
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- PDE10 MODULATORS
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The present invention relates to compounds of formula (I) wherein R1, R2, R3, R5, W, X, X1, Y, Y1, Z and Z1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used in the treatment of CNS disorders such as schizophrenia, Alzheimer's disease, and Parkinson's disease.
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Paragraph 0343-0344
(2013/03/26)
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- PDE10 MODULATORS
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The present invention relates to compounds of formula (I) wherein R1, R2, R3, R5, W, X, X1, Y, Y1, Z and Z1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used as medicaments.
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Page/Page column 61
(2013/03/26)
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- Copper-catalyzed synthesis of 1,2,4-triazoles via sequential coupling and aerobic oxidative dehydrogenation of amidines
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A convenient, efficient, and practical copper-catalyzed one-pot method for the synthesis of 1,2,4-triazoles has been developed via reactions of amidines. The procedure underwent sequential base-promoted intermolecular coupling (nucleophilic substitution) between two amidines and intramolecular aerobic oxidative dehydrogenation, and the inexpensive, convenient, and efficient method for the synthesis of 1,2,4-triazoles will attract much attention in academic and industrial research. Georg Thieme Verlag Stuttgart · New York.
- Xu, Hao,Jiang, Yuyang,Fu, Hua
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supporting information
p. 125 - 129
(2013/02/23)
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- Copper-mediated sequential C-N and N-N bond formation: Facile synthesis of symmetrical 1,2,4-triazoles
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Via a one-pot process, catalyzed by Cu(OAc)2, a series of 3,5-disubstituted 4H-1,2,4-triazoles was conveniently and efficiently synthesized by using low-toxicity, stable, readily available, inexpensive amidine hydrochloride. Georg Thieme Verlag Stuttgart New York.
- Li, Zhonglian,Zhang, Zhiguo,Zhang, Wei,Liu, Qingfeng,Liu, Tongxin,Zhang, Guisheng
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supporting information
p. 2735 - 2739
(2014/01/06)
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- Substituent effects on the electron transfer-initiated photochemical transformation of 1,2,4-triazole-substituted α-dehydroarylalaninamides into 2(1H)-quinolinone derivatives
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An investigation was undertaken to elucidate substituent effects on the photoreactivity of 1,2,4-triazole-substituted α-dehydroarylalaninamides [(Z)-1] as well as on the selectivity of 2(1H)-quinolinone derivatives (2) from a synthetic point of view. It was found that photoinduced electron transfer-initiated cyclization of (Z)-1 bearing a meta-substituted phenyl or a 4-substituted naphthalen-1-yl group in methanol proceeds with a moderate to good efficiency affording the corresponding product 2 in a selectivity ranging from 33 to 100%.
- Yazawa, Yuichi,Suzuki, Minoru,Igarashi, Tetsutaro,Sakurai, Tadamitsu
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experimental part
p. 199 - 206
(2010/05/18)
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- Synthesis of 1,2,4-Triazolines and triazoles utilizing oxazolones
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We describe herein a convenient method for the synthesis of 1,2,4-triazolines using oxazolones and azodicarboxylates. Subsequent treatment of these 1,2,4-triazolines with NaOH provides efficient access to the corresponding triazoles.
- Saleem, Rahman Shah Zaib,Tepe, Jetze J.
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experimental part
p. 4330 - 4332
(2010/09/03)
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- SMALL MOLECULE MODULATORS OF CELL ADHESION
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Compounds, particularly compounds having activity as modulators of cadherin-mediated cell adhesion having the following structure: or a pharmaceutically acceptable salt, stereoisomer or prodrug thereof, wherein R1, R2, R3,
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Page/Page column 28
(2009/12/05)
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- Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition-oxidative cyclization
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A simple one-step synthesis of 1,2,4-triazole derivatives is provided by a copper-catalyzed oxidative coupling reaction under an atmosphere of air. The process should consist of sequential N-C and N-N bond-forming copper-catalyzed oxidative coupling reactions. Starting materials and the copper catalyst are readily available and inexpensive. A wide range of functional groups are tolerated to achieve chemical diversity.
- Ueda, Satoshi,Nagasawa, Hideko
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supporting information; experimental part
p. 15080 - 15081
(2010/01/16)
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- Solid phase synthesis of 1,2,4-triazoles under microwave irradiation
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1,2,4-Triazoles (3a-g) have been prepared from three component condensation reaction of acid hydrazide (1), S-methyl isothioamide hydroiodide (2), and ammonium acetate on the surface of silica gel under microwave irradiation.
- Rostamizadeh, Shahnaz,Tajik, Hasan,Yazdanfarahi, Soheila
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p. 113 - 117
(2007/10/03)
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- Thermal rearrangement of allyl substituted unsymmetric 4H-1,2,4-triazoles to the corresponding 1H-1,2,4-triazoles
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A series of neat 4-(2-alkenyl) substituted 5-methyl-3-phenyl-4H-1,2,4- triazoles were thermolyzed at 320°C producing a rearrangement products, of which the regioisomeric 1- and 2-substituted triazoles were the main products. The group migrations were rationalized in terms of consecutive S N2-type reactions. This mechanism was supported by a study of the alkylations of the triazoles which gave similar product mixtures. 4-(2-alkenyl) substituted 3-phenyl-4H-1,2,4-triazoles, on the other hand, gave predominantly elimination products.
- Jorgensen, Kare B.,Olsen, Ragnhild B.,Carlsen, Per H.J.
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p. 481 - 495
(2007/10/03)
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- The Configuration of 1,2-Diketone Hydrazone Oximes
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The configuration of 1,2-diketone (Z)-hydrazone (E)-oximes 3a-c was determined by ring closure with formaldehyde to 1,2,4-triazine 4-oxides 5a-c and the tautomeric 4-hydroxy-1,2,4-triazines 6a-c and by Beckmann reaction to 1,2,4 triazoles 8a-c.From benzil
- Gnichtel, Horst,Toepper, Bernhard
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p. 1071 - 1074
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 3,5-DISUBSTITUED-1,2,4-TRIAZOLES
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The condensation of an acyl hydrazide and an amidine to afford an acylamidrazone, followed by thermal cyclization, provides a convenient method for preparing 3,5-disubstitued-1,2,4-triazoles in high yields.
- Francis, J. E.,Gorczyca, L. A.,Mazzenga, G. C.,Meckler, H.
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p. 5133 - 5136
(2007/10/02)
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- REACTION OF AMIDRAZONIUM IODIDES WITH β-DIKETONES
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The condensation of amidrazonium iodides with β-dicarbonyl compounds leads to salts which exist in solutions as tautomeric mixtures of the linear and cyclic forms.The position of the equilibrium depends largely on structural factors.Thermolysis of the salts is accompanied by elimination of the carbonyl compound and the formation of the corresponding 1,2,4-triazolium iodide.Alkaline treatment of the condensation products gives the free bases, which are tautomeric mixtures of the hydrazone and enehydrazine forms in solutions.The thermodynamic parameters ΔH0 and ΔS0 of the equilibrium were determined.
- Khrustalev, V. A.,Solod, O. V.,Zelenin, K. N.
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p. 444 - 453
(2007/10/02)
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- PREPARATION OF 3- AND 3,5-SUBSTITUTED 1,2,4-TRIAZOLES
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Ethyl 1,2,4-triazole-3-carboxylate (V), its 5-methyl and 5-phenyl derivatives (V and VI, respectively), 3-methyl-1,2,4-triazole (VIII), 3-phenyl-1,2,4-triazole (IX), 3,5-dimethyl-1,2,4-triazole (X), 3,5-diphenyl-1,2,4-triazole (XI) and 3-phenyl-5-methyl-1,2,4-triazole (XII) were prepared in 40-70percent yields by thermal cyclization of acylamidrazones III.
- Vanek, Tomas,Velkova, Vlasta,Gut, Jiri
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p. 2492 - 2495
(2007/10/02)
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- THE REACTIONS OF 4-PYRIMIDINONE DERIVATIVES WITH SODIUM AMIDE AND WITH HYDRAZINE: SYNTHESIS OF TRIAZOLE
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The 3,6-dialkyl-2-isopropyl-4-pyrimidinones (1)-(3) and 3,6-dimethyl-2-phenyl-4-pyrimidinone (6) were converted to the N-dealkylated 4-pyrimidinone (4), (5), and (7) by reaction with sodium amide in liq. ammonia.Also, these 4-pyrimidinones (1)-(3) and (6) were converted to the triazoles (10)-(12) by heating with hydrazine, respectively.
- Hirai, Yoshiro,Egawa, Hiroyuki,Yamada, Shoko,Yamazaki, Takao
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p. 1243 - 1246
(2007/10/02)
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- Metallhydrazide, XIX. Addition bis(diethylaluminio)substituierter Amidrazone und Carbohydrazide an Nitrile
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Amidrazones and carbohydrazides react with two equivalents of triethylaluminium to give bis(diethylaluminio) derivatives 1 and 7, respectively.In contrast to the corresponding mono(diethylaluminio) derivatives or disodium salts, these are capable of addit
- Kauffmann, Thomas,Ban, Laszlo,Kuhlmann, Dieter
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p. 3684 - 3690
(2007/10/02)
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