- Electrochemical synthesis of 1,2,4-oxadiazoles from amidoximes through dehydrogenative cyclization
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A convenient and efficient method for the generation of the iminoxy radical through anodic oxidation was developed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles fromN-benzyl amidoximes. The transformation proceeds through 1.5-Hydrogen Atom Transfer (1,5-HAT) and intramolecular cyclization. The process features simple operation, mild conditions, broad substrate scope and high functional group compatibility, and provides a facile and practical way for the preparation of 1,2,4-oxadiazoles.
- Hu, Aixi,Jiang, chan,Li, mingfang,Xu, Leitao,Ye, Jiao,Yi, Yangjie
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p. 10611 - 10616
(2021/12/27)
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- NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N?O bond formation
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A reaction involving an efficient NBS-mediated oxidative N?O bond formation has been established for the synthesis of 1,2,4-oxadiazoles from readily accessible N-acyl amidines. The features of this synthetic method include simplicity of operation, mild re
- Li, Ertong,Wang, Manman,Wang, Zhen,Yu, Wenquan,Chang, Junbiao
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p. 4613 - 4618
(2018/07/31)
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- Oxidative cyclization of amidoximes and thiohydroximic acids: A facile and efficient strategy for accessing 3,5-disubstituted 1,2,4-oxadiazoles and 1,4,2-oxathiazoles
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A facile and practical protocol has been developed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 1,4,2-oxathiazoles through oxidative cyclization of amidoximes and thiohydroximic acids, respectively at room temperature. Use of mild reaction
- Lade, Jatin J.,Patil, Bhausaheb N.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
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supporting information
p. 2103 - 2108
(2017/05/10)
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- Base-mediated one-pot synthesis of 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride without addition of extra oxidant
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A simple base-mediated one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride has been developed, in which the aldehydes act as both substrates and oxidants. The reactions include three sequential
- Wang, Wei,Xu, Hao,Xu, Yuanqing,Ding, Tao,Zhang, Wenkai,Ren, Yanrong,Chang, Haibo
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supporting information
p. 9814 - 9822
(2016/10/31)
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- A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes
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Various 3,5-disubstituted-1,2,4-oxadiazoles are smoothly formed via copper-catalyzed cascade annulation of amidines and methylarenes. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 1,2,4-oxadiazoles from easily available starting materials, with inexpensive copper catalysts and green oxidants. It has the advantages of atom- and step-economy, good functional group tolerance, as well as operational simplicity.
- Guo, Wei,Huang, Kunbo,Ji, Fanghua,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 8857 - 8860
(2015/05/20)
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- Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones
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Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60°C under an O 2 atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes
- Zhang, Feng-Lian,Wang, Yi-Feng,Chiba, Shunsuke
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p. 6003 - 6007
(2013/09/12)
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- Organic reactions in water: An efficient method for the synthesis of 1,2,4-oxadiazoles in water
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A simple and efficient process has been developed for the synthesis of 1,2,4-oxadiazoles in good yields through the reaction of amidoximes with anhydrides under catalyst-free conditions in water.
- Kaboudin, Babak,Malekzadeh, Leila
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supporting information; experimental part
p. 6424 - 6426
(2011/12/22)
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- Formation and cyclization of N′-(benzoyloxy)benzenecarboximidamides
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The formation of N′-(benzoyloxy)benzenecarboximidamides and their subsequent cyclization to 3,5-disubstituted 1,2,4-oxadiazoles in different solvents were studied. A probable reaction mechanism was proposed on the basis of the obtained results.
- Tsiulin,Sosnina,Krasovskaya,Danilova,Baikov,Kofanov
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scheme or table
p. 1874 - 1877
(2012/03/22)
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- Palladium-catalyzed carbonylative coupling of hypervalent iodonium salts with amidoximes: Synthesis of oxadiazoles
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Aryl-substituted oxadiazoles have been synthesized in one-pot procedure by the palladium-catalyzed carbonylative coupling of hypervalent iodonium salts with amidoximes under atmospheric pressure of carbon monoxide.
- Ryu, Hyung-Chul,Hong, Young-Taek,Kang, Suk-Ku
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p. 985 - 988
(2007/10/03)
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- CYCLIZATION AND ACID-CATALYZED HYDROLYSIS OF O-BENZOYLBENZAMIDOXIMES
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Kinetics of formation of 1,2,4-oxadiazoles from 24 substitution derivatives of O-benzoylbenzamidoxime have been studied in sulphuric acid and aqueous ethanol media.It has been found that this medium requires introduction of the Hammett H0 function instead of the pH scale beginning as low as from 0.1percent solutions of mineral acids.Effects of the acid concentration, ionic strength, and temperature on the reaction rate and on the kinetic isotope effect have been followed.From these dependences and from polar effects of substituents it was concluded that along with the cyclization to 1,2,4-oxadiazoles there proceeds hydrolysis to benzamidoxime and benzoic acid.The reaction is thermodynamically controlled by the acid-base equilibrium of the O-benzylated benzamidoximes.
- Grambal, Frantisek,Lasovsky, Jan
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p. 2786 - 2797
(2007/10/02)
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