2039-09-0Relevant articles and documents
A practical base mediated synthesis of 1,2,4-triazoles enabled by a deamination annulation strategy
Zhang, Chunyan,Liang, Zuyu,Jia, Xiaofei,Wang, Maorong,Zhang, Guoying,Hu, Mao-Lin
supporting information, p. 14215 - 14218 (2020/11/24)
A rapid and efficient base mediated synthesis of 1,3,5-trisubstituted 1,2,4-triazoles has been developed using the annulation of nitriles with hydrazines, which can be expanded to a wide range of triazoles in good to excellent yields. Ammonia gas is liberated during the reaction, and halo and hetero functional groups as well as free hydroxyl and amino groups are tolerated in this transformation. A variety of alkyl and aryl-substituted nitriles can be functionalized with aromatic and aliphatic hydrazines employing this procedure. This finding provides a practical and useful strategy for the synthesis of various 15N-labeled 1,2,4-triazole derivatives, and two types of mGlu5 receptor pharmaceuticals can be easily assembled in a one-pot manner. This journal is
One pot solvent-free solid state synthesis, photophysical properties and crystal structure of substituted azole derivatives
Du, Yanting,Wan, Zilu,Chen, Lianqing,Wu, Lamei
, p. 315 - 325 (2019/05/27)
A solvent-free solid state method has been developed to synthesize three series of substituted azole derivatives (including 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole) in high yields by condensation cyclization of N,N′-bishydrazide derivatives with corresponding cyclization agents, respectively. This general method avoids the use of organic solvents, saves cost and resources, simplifies post-processing and increases reaction rates. These compounds have been fully characterized by 1H NMR, 13C NMR, elemental analysis and MS. The structure of 2,5-di (4-tertbutylphenyl)-1,3,4-oxadiazole has been determined by single crystal X-ray diffraction analysis. The cell parameters are as follows: monoclinic crystal system, Cc space group, a = 18.735 (2) ?, b = 6.3375 (8) ?, c = 16.824 (2) ? and α = γ = 90°; β = 98.292 (2). The electronic absorption and fluorescent properties of these compounds have been systematically investigated for the first time. The relationships between heterocyclic structures and photophysical properties have been discussed. The alteration of emission and absorption wavelengths can be elucidated by hybrid atoms' electronegativity and Substituents' Hammett constants. This approach proposes a novel insight to provide a great number of novel substituted azole derivatives with good photophysical properties by a general green method.
I2 mediated one-pot synthesis of 1,2,4-triazoles from amidines and imidates
Inturi, Surendra Babu,Kalita, Biswajit,Ahamed, A. Jafar
supporting information, p. 2227 - 2230 (2016/05/10)
A one-pot facile synthesis of 3,5-disubstituted-1H-1,2,4-triazole derivatives using I2/Cs2CO3 has been described. The method involves readily available inexpensive reagents and is applicable to a wide range of substrates.
Copper-catalyzed one-pot synthesis of 1,2,4-triazoles from nitriles and hydroxylamine
Xu, Hao,Ma, Shuang,Xu, Yuanqing,Bian, Longxiang,Ding, Tao,Fang, Xiaomin,Zhang, Wenkai,Ren, Yanrong
, p. 1789 - 1794 (2015/02/19)
A simple and efficient copper-catalyzed one-pot synthesis of substituted 1,2,4-triazoles through reactions of two nitriles with hydroxylamine has been developed. The protocol uses simple and readily available nitriles and hydroxylamine hydrochloride as th
Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates
Sudheendran, Kavitha,Schmidt, Dietmar,Frey, Wolfgang,Conrad, Jürgen,Beifuss, Uwe
, p. 1635 - 1645 (2014/02/14)
Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)2-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K3[Fe(CN)6]/ atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4- triazoles with yields up to 64% rests on the Cu(OTf)2-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step.
SUBSTITUTED TRIAZOLES AND THEIR USE FOR TREATMENT AND/OR PREVENTION NEUROLOGICAL AND PSYCHIATRIC DISORDERS
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Page/Page column 66, (2013/07/31)
This invention relates to compounds of formula (I), their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, Ar, R1, R2, R3 have meanings given in the description.
NOVEL COMPOUNDS
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Paragraph 0340; 0341; 0342, (2013/07/25)
This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, Ar, R1, R2, R3 have meanings given in the description.
Liquid-phase traceless synthesis of 3,5-disubstituted 1,2,4-triazoles
Wang, Xi-Cun,Wang, Jun-Ke,Wu, Dong-Qing,Zong, Ying-Xiao
, p. 2595 - 2598 (2007/10/03)
A liquid-phase traceless route to 3,5-disubstituted-1,2,4-triazoles has been developed, which allows for the incorporation of two elements of diversity. The heterocycle was constructed upon PEG6000 (soluble polymer) modified by 4-hydroxy-2-methoxy-benzaldehyde, from which a traceless cleavage could be realized with TFA-CH2Cl2. This method provided a library of 3,5-disubstituted-1,2,4-triazoles with high yields and purity. Georg Thieme Verlag Stuttgart.
An improved procedure for the deamination of symmetrical 3,5-disubstituted 4-amino-1,2,4-triazoles
Bentiss, Fouad,Lagrenee, Michel,Vezin, Herve,Bouanis, Marya,Mernari, Bouchaib
, p. 93 - 96 (2007/10/03)
A number of symmetrical 3,5-disubstituted-4H-1,2,4-triazoles have been synthesized in good yields by deamination of the corresponding 4-amino-1,2,4-triazoles via reductive diazotation of these amino compounds in the presence of hypophosphorous acid. Analy
