- Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles
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Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.
- Wang, Xuetong,Wang, Yin,Liu, Xiaoling,He, Tingshu,Li, Lingli,Wu, Huili,Zhou, Shangjun,Li, Dan,Liao, Siwei,Xu, Ping,Huang, Xing,Yuan, Jianyong
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supporting information
(2021/10/14)
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- Efficient insecticidal aerosol and preparation method thereof
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The invention provides an efficient insecticidal aerosol, which comprises the following components in percentage by weight: 0.1-0.5wt% of a component A, i.e. a 1, 2, 4-diazole derivative shown as a formula I, 1-1.5wt% of a component B, i.e. a marigold ext
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Paragraph 0058; 0069-0071; 0076-0077
(2020/10/30)
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- Preparation, structure, and versatile reactivity of pseudocyclic benziodoxole triflate, new hypervalent iodine reagent
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A new pseudocyclic triflate derivative of benziodoxole (IBA-OTf) was prepared and characterized by X-ray analysis. This highly electrophilic reagent readily reacts with various organic substrates to give the corresponding products in good yields. Furthermore, IBA-OTf can be used as a catalyst with m-chloroperoxybenzoic acid as the terminal oxidant. This journal is
- Yoshimura, Akira,Nguyen, Khiem C.,Klasen, Scott C.,Saito, Akio,Nemykin, Victor N.,Zhdankin, Viktor V.
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supporting information
p. 7835 - 7838
(2015/05/13)
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- One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acids using 4-(dimethylamino)pyridinium acetate as efficient, regenerable, and green catalyst with ionic liquid character
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A recyclable bifunctional acid-base organocatalyst with ionic liquid character has been prepared and its catalytic activity for the preparation of oxadiazoles has been investigated.
- Nowrouzi, Najmeh,Khalili, Dariush,Irajzadeh, Maryam
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p. 801 - 806
(2015/03/18)
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- Efficient and convenient protocol for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using HClO4-SiO2 as a heterogeneous recyclable catalyst
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Silica-supported perchloric acid (HClO4SiO2) was found to be a new, highly efficient, inexpensive, and reusable catalyst for a rapid and efficient synthesis of various 1,2,4-oxadiazoles with good to excellent yields under solvent-free conditions. The present methodology has been effectively utilized for the synthesis of oxolamine, an anti-inflammatory drug.
- Tadikonda, Ramu,Nakka, Mangarao,Gajula, Mahaboob Basha,Rayavarapu, Srinuvasarao,Gollamudi, Padma Rao,Vidavalur, Siddaiah
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supporting information
p. 1978 - 1986
(2014/07/07)
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- Br?nsted acid-catalyzed simple and efficient synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles using 2,2,2-trichloroethyl imidates in PEG
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A facile and highly efficient synthesis of 3,4,5-trisubstituted 1,2,4-triazoles and 3,5-disubstituted 1,2,4-oxadiazoles from 2,2,2-trichloroethyl imidates using PEG as a solvent and employing PTSA as the catalyst under mild conditions is described.
- Mangarao, Nakka,Mahaboob Basha, Gajula,Ramu, Tadikonda,Srinuvasarao, Rayavarapu,Prasanthi, Sarakula,Siddaiah, Vidavalur
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supporting information
p. 177 - 179
(2014/01/06)
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- A novel, one-pot, three-component synthesis of 1,2,4-oxadiazoles under microwave irradiation and solvent-free conditions
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A novel synthesis of 3,5-disubstituted 1,2,4-oxadiazoles is described from a one-pot, three-component reaction between nitriles, hydroxylamine, and Meldrum's acids under microwave irradiation and solvent-free conditions in good to excellent yields. Georg
- Adib, Mehdi,Mahdavi, Mohammad,Mahmoodi, Niusha,Pirelahi, Hooshang,Bijanzadeh, Hamid Reza
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p. 1765 - 1767
(2008/02/04)
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- Electrochemical oxidation of substituted amide oximes and 4,5-dihydro-1,2,4-oxadiazoles
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The electrooxidation of several substituted amide oximes to yield the corresponding nitriles, alcohols, and imidate was successfully carried out. The reaction products were dependent on the substituents. Additionally, 4,5-dihydro-1,2,4-oxadiazoles derived from amide oximes were electro-oxidized to afford 1,2,4-oxadiazoles in good yields.
- Okimoto, Mitsuhiro,Takahashi, Yukio
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p. 427 - 428
(2007/10/03)
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- A Simplified Procedure for Preparing 3,5-Disubstituted-1,2,4-Oxadiazoles by Reaction of Amidoximes with Acyl Chlorides in Pyridine Solution
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3-R-5-R'-1,2,4-Oxadiazoles are prepared in fair to good yield by short-time, one-pot reaction of an amidoxime, RC(NH2)NOH, with an acyl chloride, R'COCl, in pyridine solution.Precipitation of the oxadiazole occurs on diluting the pyridine reaction solutio
- Chiou, Shishue,Shine, Henry J.
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p. 125 - 128
(2007/10/02)
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- Direct Synthesis of 5-Methyl-3-aryl-1,2,4-oxadiazoles from Aryl Aldehydes, Nitroethane, and Ammonium Acetate
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The condensation of 2,5-dimethoxybenzaldehyde (1b) with nitroethane and ammonium acetate in glacial acetic acid has been found to give three diffrent products, depending on reactant ratio and reaction time.At an aldehyde:nitroethane:ammonium acetate ratio of 1:1.5:0.8 a normal Knoevenagel condensation occured, yielding 1-(2,5-dimethoxyphenyl)-2-nitropropene.At a reactant ratio of 1:3:2 (same reactant sequence), the primary product was 2,5-dimethoxybenzonitrile, and at a reactant ratio of 1:40:8, with extended reflux time, the major product was 3-(2,5-dimethoxyphenyl)-5-methyl-1,2,4-oxadiazole (8b).This last reaction served as a prototype for a new oxadiazole synthesis which was then extended to include six additional 5-methyl-3-aryl-1,2,4-oxadiazoles (8a,c-g; where aryl = Ph, 2,5-dimethoxyphenyl, 2,4-dichlorophenyl, m-chlorophenyl, p-tolyl, 3,5-dimethoxyphenyl, and p-carboxyphenyl), whose structures were assigned on the basis of 13C NMR characteristics of known reference compounds.Benzonitrile also reacted with excess nitroethane and ammonium acetate to yield 5-methyl-3-phenyl-1,2,4-oxadiazole (8a).The overall mechanism of oxadiazole formation is shown to be dependent on a preliminary reaction wherein the nitroalkane, in the presence of ammonium acetate and acetic acid, is first transformed into the corresponding alkanoic acid and hydroxylamine.Hydroxylamine then converts the aromatic aldehyde, via the intermediary nitrile, to the oxadiazoles following reactions of established precedent.
- Young, Thomas E.,Beidler, William Thomas
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p. 1182 - 1186
(2007/10/02)
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- Formation and Thermal Reaction of O-(N-Acetylbenzimidoyl)benzamidoxime: Comparison with the Formation of 3,5-Disubstituted 1,2,4-Oxadiazoles from O-Acetylarylamidoximes and O-Aroylacetamidoximes
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Salts of O-(benzimidoyl)benzamidoxime have been obtained by the action of N-chloro- or N-bromo-succinimide, or the halogens, on benzamidoxime.Acetylation of the free base gave the title compound, which underwent a thermal cyclisation, with loss of acetamide, to give 3,5-diphenyl-1,2,4-oxadiazole.The mechanism of the reaction, in diphenyl ether, closely paralleled the thermal cyclisation of O-acetylarylamidoximes and O-aroylacetamidoximes, and is thought to involve a polar cyclisation step followed by rate-determining proton transfer. 13C N.m.r. spectra for 32 oxime, amidoxime, O-acetylamidoxime, 5-methyl-1,2,4-oxadiazol-3-yl, and 3-methyl-1,2,4-oxadiazol-5-yl groups on the phenyl ring are calculated.
- Ooi, Ngan Sim,Wilson, David A.
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p. 1792 - 1799
(2007/10/02)
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