- Iodine Catalyzed Oxidative Coupling of Diaminoazines and Amines for the Synthesis of 3,5-Disubstituted-1,2,4-Triazoles
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A simple, convenient, transition metal-free one pot synthesis of 3,5-disubstituted-1,2,4-triazoles has been established. The innovation in this reaction is the use of easily available 1,1-diaminoazines as substrates. This method provides the products with wider substrate scope, at an expedited rate, and with relatively better yields in comparison to the reported methods. The reaction mechanism involves an initial intermolecular nucleophilic addition (facilitated by I2) followed by intramolecular nucleophilic cyclization.
- Beifuss, Uwe,Bharatam, Prasad V.,Chourasiya, Sumit S.,Kathuria, Deepika,Sahoo, Subash C.,Wani, Aabid A.
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p. 7659 - 7671
(2021/06/25)
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- One pot solvent-free solid state synthesis, photophysical properties and crystal structure of substituted azole derivatives
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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.
- Du, Yanting,Wan, Zilu,Chen, Lianqing,Wu, Lamei
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p. 315 - 325
(2019/05/27)
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- I2 mediated one-pot synthesis of 1,2,4-triazoles from amidines and imidates
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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.
- Inturi, Surendra Babu,Kalita, Biswajit,Ahamed, A. Jafar
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supporting information
p. 2227 - 2230
(2016/05/10)
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- Copper-catalyzed one-pot synthesis of 1,2,4-triazoles from nitriles and hydroxylamine
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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
- Xu, Hao,Ma, Shuang,Xu, Yuanqing,Bian, Longxiang,Ding, Tao,Fang, Xiaomin,Zhang, Wenkai,Ren, Yanrong
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p. 1789 - 1794
(2015/02/19)
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- Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates
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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.
- Sudheendran, Kavitha,Schmidt, Dietmar,Frey, Wolfgang,Conrad, Jürgen,Beifuss, Uwe
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p. 1635 - 1645
(2014/02/14)
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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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- 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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- Liquid-phase traceless synthesis of 3,5-disubstituted 1,2,4-triazoles
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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.
- Wang, Xi-Cun,Wang, Jun-Ke,Wu, Dong-Qing,Zong, Ying-Xiao
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p. 2595 - 2598
(2007/10/03)
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- An improved procedure for the deamination of symmetrical 3,5-disubstituted 4-amino-1,2,4-triazoles
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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
- Bentiss, Fouad,Lagrenee, Michel,Vezin, Herve,Bouanis, Marya,Mernari, Bouchaib
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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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