- Convenient one-pot synthesis of 1,2,4-oxadiazoles and 2,4,6-triarylpyridines using graphene oxide (GO) as a metal-free catalyst: Importance of dual catalytic activity
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A convenient and efficient process for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 2,4,6-triarylpyridines has been described using an inexpensive, environmentally benign, metal-free heterogeneous carbocatalyst, graphene oxide (GO). GO plays a dual role of an oxidizing agent and solid acid catalyst for synthesizing 1,2,4-oxadiazoles and triarylpyridines. This dual catalytic activity of GO is due to the presence of oxygenated functional groups which are distributed on the nanosheets of graphene oxide. A broad scope of substrate applicability and good sustainability is offered in this developed protocol. The results of a few control experiments reveal a plausible mechanism and the role of GO as a catalyst was confirmed by FTIR, XRD, SEM, and HR-TEM analysis.
- Basak, Puja,Dey, Sourav,Ghosh, Pranab
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p. 32106 - 32118
(2021/12/02)
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- 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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- One-pot synthesis of 3,5-diaryl substituted-1,2,4-oxadiazoles using gem -dibromomethylarenes
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1,2,4-Oxadiazole is one of the most promising heterocyclic ring systems in medicinal chemistry. In the present paper, we report the method for an efficient one-pot synthesis of 3,5-diaryl substituted 1,2,4-oxadiazoles using a two-component reaction of gem-dibromomethylarenes with amidoximes in good yields. In this method, gem-dibromomethylarenes are used as benzoic acid equivalents for the efficient synthesis of aryl-substituted 1,2,4-oxadiazoles. It is anticipated that this methodology will have versatile applications in the practical syntheses of various molecules of both medicinal and material chemistry importance.
- Vinaya, Kambappa,Chandrashekara, Ganganahalli K.,Shivaramu, Prasanna D.
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p. 690 - 696
(2019/09/06)
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- METHOD FOR PRODUCING 1,2,4-OXADIAZOLE DERIVATIVE
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The invention provides a production method of a 1,2,4-oxadiazole derivative represented by formula (A), which comprises reacting a compound represented by formula (B) and a compound represented by formula (C) in the presence of a basic compound: wherein Ar is an aromatic group or an aromatic group having substituent(s); W, X, Y and Z are each independently —S—, —N═, —CH═ or —CR═, and one selected from W, X, Y and Z is —S—; and R is an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms or a halogen atom.
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Paragraph 0144
(2018/03/01)
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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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- Synthesis of 1,2,4-Oxadiazoles via DDQ-Mediated Oxidative Cyclization of Amidoximes
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An oxidative cyclization of amidoximes to form 1,2,4-oxadiazoles, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), is described. A range of alkyl, aryl, and heteroaryl substrates are tolerated under these conditions. This reaction serves as an alternate approach for the synthesis of functionally diverse oxadiazoles via a rapid and straightforward synthetic procedure.
- Parker, Patrick D.,Pierce, Joshua G.
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p. 1902 - 1909
(2016/06/15)
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- PROCESSES FOR THE PREPARATION OF 3,5-DISUBSTITUTED-1,2,4-OXADIAZOLES
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Provided herein are processes for the preparation of 3,5-disubstituted-1,2,4-oxadiazoles and salts thereof comprising reacting a N-hydroxyamidine with an acyl chloride in a reaction mixture comprising a water-immiscible organic solvent and an aqueous base
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- HNO made-easy from photochemical cycloreversion of novel 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides
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A variety of symmetric and asymmetric 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides have been prepared through cycloaddition of aromatic and heteroaromatic nitrile oxides to heteroaromatic amidoximes. A library of novel, fully characterized, 1,
- Memeo, Misal Giuseppe,Dondi, Daniele,Mannucci, Barbara,Corana, Federica,Quadrelli, Paolo
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p. 7387 - 7394
(2013/08/23)
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- PHARMACEUTICAL COMPOSITIONS
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This invention relates to novel pharmaceutical compositions comprising therapeutically effective combination of a positive allosteric modulator of nicotine receptors; and a cognitive enhancer selected from the group consisting of a nicotine acetylcholine
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Page/Page column 14-15
(2008/06/13)
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- NOVEL OXADIAZOLE DERIVATIVES AND THEIR MEDICAL USE
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This invention relates to novel oxadiazole derivatives of formula (I) which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of disease
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Page/Page column 20
(2008/06/13)
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