- 1,2-Dibenzoylhydrazine
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In the crystal structure of the title compound, C14H12N2O2, the molecule lies about a twofold axis; two carbonyl groups and the H atoms of the N-N bond are in a trans orientation with respect to each other. In the crystal, each molecule is linked to the other and vice versa by intermolecular N-H···O hydrogen bonds between the amide hydrogen and the O atoms of neighbouring molecules to form two ten-membered rings, each of which has the graph-set motif C4R22(10). This extends as a polymeric chain along the c axis.
- Shanmuga Sundara Raj,Yamin, Bohari M.,Boshaala, Ahmed M. A.,Tarafder,Crouse, Karen A.,Fun, Hoong-Kun
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Read Online
- N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
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A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
- Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
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supporting information
p. 17713 - 17721
(2021/11/10)
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- A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles
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N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is
- Yavari, Issa,Khaledian, Omid
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supporting information
p. 9150 - 9153
(2020/10/02)
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- Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media
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Herein, we report an atom-efficient, rapid, green, and sustainable approach to synthesize isoquinolines and isoquinolinones using a homogeneous recyclable ruthenium catalyst in PEG Media assisted by microwave energy. Dibenzoylhydrazine was used for C–H/N–N activation reactions for the first time in combination with ketazine as oxidizing directing groups for annulation reactions with internal alkynes. The developed protocol is environmentally benign due to significantly shortened times with an easy extraction method, higher atom economy, external oxidant and silver or antimony salt free conditions, applicability to a gram scale synthesis, use of biodegradable solvent and wide substrate scope with higher product yields. Moreover, it is worth noting that the established methodology allowed reuse of the catalytic system for up to five successive runs with minimal loss in activity.
- Deshmukh, Dewal S.,Gangwar, Neha,Bhanage, Bhalchandra M.
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p. 2919 - 2927
(2019/05/10)
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- Continuous hydrazide preparation method
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The invention relates to a continuous hydrazide preparation method. The preparation method includes: in a micro-channel reactor or a pipeline reactor, subjecting esters, anhydrides or acyl chloride tocontinuous reaction with hydrazine or solution of hydrazine under a solvent-free condition or in a solvent to prepare a hydrazide compound. The preparation method is simple, short in technical process, less in waste gas, wastewater and industrial residues, beneficial to environmental production and suitable for industrial production. The adopted reactor is short in reaction time, high in safety and capable of realizing continuous production. The adopted reactor is high in workshop space utilization rate, and large-scale production can be realized. By adoption of the preparation method, solvent recycling can be realized, and production cost is reduced; in addition, high raw material conversion rate, high quality stability and high purity are realized.
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Paragraph 0063-0065
(2019/04/17)
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- N-Methoxyamide: An Alternative Amidation Reagent in the Rhodium(III)-Catalyzed C-H Activation
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In the field of transition-metal-catalyzed C-H activation, N-methoxyamides are widely used as C-H activation substrate. Unexpectedly, in this work N-methoxyamides were found to work as efficient amidation reagents in the rhodium(III)-catalyzed C-H activation with boric acid as a cocatalyst. This reaction features broad substrate scope and good yields.
- Zhou, Chao,Zhao, Junqi,Guo, Weicong,Jiang, Jijun,Wang, Jun
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supporting information
p. 9315 - 9319
(2019/11/28)
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- Synthesis and in vitro urease inhibitory activity of benzohydrazide derivatives, in silico and kinetic studies
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Benzohydrazide derivatives 1–43 were synthesized via “one-pot” reaction and structural characterization of these synthetic derivatives was carried out by different spectroscopic techniques such as 1H NMR and EI-MS. The synthetic molecules were evaluated for their in vitro urease inhibitory activity. All synthetic derivatives showed good inhibitory activities in the range of (IC50 = 0.87 ± 0.31–19.0 ± 0.25 μM) as compared to the standard thiourea (IC50 = 21.25 ± 0.15 μM), except seven compounds 17, 18, 23, 24, 29, 30, and 41 which were found to be inactive. The most active compound of the series was compound 36 (IC50 = 0.87 ± 0.31 μM) having two chloro groups at meta positions of ring A and methoxy group at para position of ring B. The structure–activity relationship (SAR) of the active compounds was established on the basis of different substituents and their positions in the molecules. Kinetic studies of the active compounds revealed that compounds can inhibit enzyme via competitive and noncompetitive modes. In silico study was also performed to understand the binding interactions of the molecules (ligand) with the active site of enzyme.
- Abbas, Azhar,Ali, Basharat,Kanwal,Khan, Khalid Mohammed,Iqbal, Jamshed,ur Rahman, Shafiq,Zaib, Sumera,Perveen, Shahnaz
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p. 163 - 177
(2018/10/21)
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- Synthesis of acylhydrazines and, symmetrical and asymmetrical diacylhydrazines from carboxylic acid via the Vilsmeier reagent mediated process
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(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) has been used as an efficient and convenient reagent for the one-pot synthesis of acylhydrazines and symmetrical and asymmetrical diacylhydrazines from carboxylic acids. This reaction proceeded smoothly under mild conditions and it is quite practical, since the starting carboxylic acids can be easily handled and stored. Cleanliness, simplicity of the method and good to excellent yield of products are other advantages of this method.
- Zarei, Maaroof,Nakhli, Maliheh Eslami
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p. 1909 - 1918
(2017/02/15)
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- One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent
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A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology for 1,3,4-thiadiazole synthesis has the advantage of simplicity, ambient reaction conditions, easy purification and good to excellent yield of products.
- Zarei, Maaroof
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p. 1867 - 1872
(2017/03/11)
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- One-Pot Catalytic Approach for the Selective Aerobic Synthesis of Imines from Alcohols and Amines Using Efficient Arene Diruthenium(II) Catalysts under Mild Conditions
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A green and efficient catalytic approach for the selective synthesis of imines in air at room temperature was achieved with the aid of newly synthesised diruthenium(II) complexes [(η6-p-cymene)2Ru2Cl2(μ-L)] containing substituted 1,2-diacylhydrazine ligands. All the new complexes were fully characterised by analytical and spectroscopic techniques. The solid-state structure of a representative complex was solved by single-crystal X-ray diffraction analysis. The diruthenium(II) complexes also enable the selective aerobic oxidation of alcohols to aldehydes. The catalytic reaction operates in the presence of air as a green and cheap oxidant, and releases water as the only by-product. A plausible mechanism is proposed for the imine formation, which is believed to proceed via an aldehyde intermediate.
- Saranya, Sundar,Ramesh, Rengan,Grzegorz Ma?ecki, Jan
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p. 6726 - 6733
(2017/12/07)
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- [3+3]-cycloaddition of donor-acceptor cyclopropanes with nitrile imines generated in situ: Access to tetrahydropyridazines
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Donor-acceptor cyclopropanes are reacted under the influence of a Lewis acid with hydrazonyl chlorides to afford tetrahydropyridazines. Formally, this transformation can be regarded as a [3 + 3]-cycloaddition of three-membered rings and nitrile imines generated in situ. This efficient method provides fast access to a variety of structurally diverse pyridazine derivatives. The structure of a typical product was confirmed by X-ray crystallography.
- Garve, Lennart K. B.,Petzold, Martin,Jones, Peter G.,Werz, Daniel B.
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supporting information
p. 564 - 567
(2016/02/18)
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- Direct oxidative amidation of aldehydes with amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions via a dual-catalysis process
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A simple and efficient procedure for the synthesis of amides directly from aldehydes and amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights. The proposed dual-catalysis mechanistic pathway was briefly investigated. Furthermore, the heteropolyanion-based ionic liquids were easily reusable for this oxidative amidation.
- Fu, Renzhong,Yang, Yang,Zhang, Jin,Shao, Jintao,Xia, Xuming,Ma, Yunsheng,Yuan, Rongxin
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p. 1784 - 1793
(2016/02/10)
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- Organometallic complex and light-emitting element, light emitting device and electronic device (by machine translation)
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A first object is to provide an organometallic complex capable of exhibiting phosphorescence. In General Formula (G1), at least one substituent of R11 to R14 represents any of a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a cyano group. At least one substituent of R15 to R19 represents any of a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a cyano group. R20 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 4 to 10 carbon atoms. M is either a Group 9 element or a Group 10 element. When M is a Group 9 element, n is 3, and when M is a Group 10 element, n is 2.
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Paragraph 0181; 0182
(2017/01/02)
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- In situ generated cetyltrimethylammonium bisulphate in choline chloride-urea deep eutectic solvent: A novel catalytic system for one pot synthesis of 1,3,4-oxadiazole
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Cetyltrimethylammonium bisulphate ([CTA]HSO4) catalysed one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles from carboxylic acid and acid hydrazide in biodegradable deep eutectic solvent is investigated. [CTA]HSO 4 is generated in situ from cetyltrimethylammonium peroxodisulphate. Cyclization of diacylhydrazide using [CTA]HSO4 gives best alternative to traditional dehydration agents. Its remarkable features include a milder procedure, simplicity in workup and purification, good to excellent yields of products, use of inexpensive, recyclable reagents, and eco-friendly aspects by avoiding toxic catalysts/reagents and solvents. Graphical Abstract: [Figure not available: see fulltext.].
- More, Priyanka Anant,Gadilohar, Balu Laxman,Shankarling, Ganapati Subray
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p. 1393 - 1398
(2014/08/18)
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- Stability or flexibility: Metal nanoparticles supported over cross-linked functional polymers as catalytic active sites for hydrogenation and carbonylation
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A novel cross-linked functional polymer was prepared through copolymerization between 1, 3, 4, 6-tetraallylglycoluril and 4-vinyl pyridine. Pt and Pd nanoparticles supported over this polymeric framework (Pt/CFP and Pd/CFP) were detailedly characterized by TEM, EDS, and XPS. Pt nanoparticles were kept in the monodispersed state with the average size of 1.4 nm. Monodispersed Pd nanoparticles were about 4.5 nm. The hydrogenation of nitrobenzenes over Pt/CFP shows high activity and selectivity with the substrate to Pt ratio of 4000 under mild reactions. Pd/CFP was the catalyst for carbonylation of aryl iodides in the presence of secondary amines and acylhydrazines. Double carbonylation with secondary amines produced α-ketoamides with the selectivity of 80%. Diacylhydrazine molecules were synthesized by the direct carbonylation of aryl iodide with acylhydrazine over Pd/CFP. The recyclability and recoverability of Pt/CFP were investigated through a seven-run recycling test of nitrobenzene hydrogenation. The flexibility of Pd/CFP in the carbonylation process was thoroughly explored by a 12-run recycling test. Supported Pt or Pd nanoparticles showed the macroscopic robustness in their catalytic performance in the catalytic cycle. The flexibility of metal nanoparticles and the polymeric supports guaranteed macroscopic catalytic robustness.
- Chen, Bingfeng,Li, Fengbo,Huang, Zhijun,Lu, Tao,Yuan, Guoqing
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- A general and efficient entry to asymmetric tetrazines for click chemistry applications
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The importance of click chemistry is widely recognized. Among all the known click reactions, those involving tetrazines represent the fastest click reactions reported and are generating a great deal of interest. However, there is no efficient entry to asymmetric tetrazines and those with strong electron withdrawing groups, which limits the development of this field. Herein, we report a general and efficient entry to asymmetric tetrazines with strongly electron withdrawing groups.
- Wang, Danzhu,Chen, Weixuan,Zheng, Yueqin,Dai, Chaofeng,Wang, Lifang,Wang, Binghe
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p. 171 - 177
(2013/09/02)
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- Triazole derivative, and light-emitting element, light-emitting device, and electronic device using triazole derivative
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A novel triazole derivative which has a large energy gap and can be used for electron-transporting layer of a light-emitting element or as a host material. In addition, a light-emitting element which has higher emission efficiency by using the novel triazole derivative. Furthermore, a low power consumption light-emitting device and electronic device. A triazole derivative having a structure represented by the formula (G1). In the formula, Py represents a pyridyl group. R11 and R12 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group.
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- Synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using [Et 2NSF2]BF4 as a practical cyclodehydration agent
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The preparation of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using XtalFluor-E ([Et2NSF2]BF4) as cyclodehydration reagent is described. Various functionalized 1,3,4-oxadiazoles were synthesized and it was found that the use of acetic acid as an additive generally improved the yields.
- Pouliot, Marie-France,Angers, Laetitia,Hamel, Jean-Denys,Paquin, Jean-Francois
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supporting information; experimental part
p. 988 - 993
(2012/04/10)
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- Oxadiazoles in medicinal chemistry
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Oxadiazoles are five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom, and they exist in different regioisomeric forms. Oxadiazoles are frequently occurring motifs in druglike molecules, and they are often used with the intention of being bioisosteric replacements for ester and amide functionalities. The current study presents a systematic comparison of 1,2,4- and 1,3,4-oxadiazole matched pairs in the AstraZeneca compound collection. In virtually all cases, the 1,3,4-oxadiazole isomer shows an order of magnitude lower lipophilicity (log D), as compared to its isomeric partner. Significant differences are also observed with respect to metabolic stability, hERG inhibition, and aqueous solubil ity, favoring the 1,3,4-oxadiazole isomers. The difference in profile between the 1,2,4 and 1,3,4 regioisomers can be rationalized by their intrinsically different charge distributions (e.g., dipole moments). To facilitate the use of these heteroaromatic rings, novel synthetic routes for ready access of a broad spectrum of 1,3,4-oxadiazoles, under mild conditions, are described.
- Bostr?m, Jonas,Hogner, Anders,Llinàs, Antonio,Wellner, Eric,Plowright, Alleyn T.
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scheme or table
p. 1817 - 1830
(2012/05/05)
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- A convenient and simple transformation of acid hydrazides to N,N′-diacylhydrazines with Hg(OAc)2 under solid state conditions
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A highly efficient and practical methodology for the transformation of acid hydrazides 1 to N,N′-diacylhydrazines 2 is described under solid state conditions at RT utilizing inexpensive and easily available reagent Hg(OAc) 2. The products are obtained in good yields with high purity.
- Mogilaiah,Anitha,Shiva Kumar,Shiva Prasad
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experimental part
p. 126 - 128
(2011/03/21)
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- ORGANOMETALLIC COMPLEX, LIGHT-EMITTING ELEMENT, DISPLAY DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE
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Provided are organometallic complexes that can exhibit phosphorescence. One of the novel organometallic complexes is represented by General Formula (G1). In General Formula (G1), R1 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aralkyl group having 7 to 10 carbon atoms which may have a substituent. In addition, R2 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aryl group having 6 to 12 carbon atoms which may have a substituent. Further, Ar represents an arylene group having 6 to 13 carbon atoms which may have a substituent. Further, M represents a Group 9 element or a Group 10 element.
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Page/Page column 76-77
(2011/05/11)
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- Use of acylhydrazine- and acylhydrazone-type ligands to promote CuI-catalyzed C-N cross-coupling reactions of aryl bromides with N-heterocycles
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A series of ten acylhydrazine- and acylhydrazone-type ligands were designed and synthesized. Their electronic and steric properties were easily modified and tuned by varying the substituents in the vicinity of the acylhydrazine and acylhydrazone units. The effect of ligands on the catalytic activity of Ullmann reactions was assessed by using a combination of these ligands with CuI. The catalytic system is very efficient for the C-N coupling reaction of azoles with aryl and heteroaryl bromides. A simple and efficient procedure for copper-catalyzed C-N cross-coupling reactions between aryl bromides and NH-containingheterocycles is illustrated. Readily available acylhydrazine- and acylhydrazone-typeligands promote the reaction.
- Li, Liuyi,Zhu, Lei,Chen, Dagui,Hu, Xuelei,Wang, Ruihu
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supporting information; experimental part
p. 2692 - 2696
(2011/06/25)
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- Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride
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N-N bond cleavage in hydrazines is widely used in the preparation of amines and thus occupies a significant place in organic synthesis. In this paper, we report a new method for the reductive cleavage of N-N bonds in hydrazines by commercially available and cheap aqueous titanium(iii) trichloride. The reaction proceeds smoothly under a broad pH range from acidic to neutral and basic conditions to afford amines in good yields. This method is compatible with substrates containing functionalities such as C-C double bonds, benzyl-nitrogen bonds, benzyloxy and acyl groups. The Royal Society of Chemistry 2011.
- Zhang, Yan,Tang, Qiang,Luo, Meiming
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supporting information; experimental part
p. 4977 - 4982
(2011/08/05)
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- 17O NMR studies of substituted 1,3,4-oxadiazoles
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Three series of substituted 1,3,4-oxadiazoles were studied by 17O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.
- Gierczyk, Blazej,Zalas, MacIej,Kazmierczak, Marcin,Grajewski, Jakub,Pankiewicz, Radoslaw,Wyrzykiewicz, Bozena
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experimental part
p. 648 - 654
(2012/01/06)
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- ORGANOMETALLIC COMPLEX AND LIGHT-EMITTING ELEMENT, LIGHTING DEVICE, AND ELECTRONIC DEVICE INCLUDING THE ORGANOMETALLIC COMPLEX
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A first object is to provide an organometallic complex capable of exhibiting phosphorescence. In General Formula (G1), at least one substituent of R11 to R14 represents any of a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a cyano group. At least one substituent of R15 to R19 represents any of a halogen group, a haloalkyl group having 1 to 4 carbon atoms, and a cyano group. R20 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 4 to 10 carbon atoms. M is either a Group 9 element or a Group 10 element. When M is a Group 9 element, n is 3, and when M is a Group 10 element, n is 2.
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- Mild and convenient one-pot synthesis of 1,3,4-oxadiazoles
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A mild, general, convenient, and efficient one-pot synthesis of 2-phenyl-5-substituted-1,3,4-oxadiazoles is described. Both (hetero)aryl and alkyl carboxylic acids were efficiently condensed with benzohydrazide in the presence of TBTU to give diacylhydrazine intermediates. The latter underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted- 1,3,4-oxadiazoles in good to very good yields.
- Stabile, Paolo,Lamonica, Alessandro,Ribecai, Arianna,Castoldi, Damiano,Guercio, Giuseppe,Curcuruto, Ornella
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supporting information; experimental part
p. 4801 - 4805
(2010/10/02)
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- Molecular logic gates and switches based on 1,3,4-oxadiazoles triggered by metal ions
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Organic molecular devices for information processing applications are highly useful building blocks for constructing molecular-level machines. The development of "intelligent" molecules capable of performing logic operations would enable molecular-level devices and machines to be created. We designed a series of 2,5-diaryl-1,3,4oxadiazoles bearing a 2-(para-substituted) phenyl and a 5-(o-pyridyl) group (substituent X = NMe2, OEt, Me, H, and Cl; 1a-e) that form a bidentate chelating environment for metal ions. These compounds showed fluorescence response profiles varying in both emission intensity and wavelength toward the tested metal ions Ni2+, Cu 2+, Zn2+, Cd2+, Hg2+, and Pb 2+ and the respons-es were dependent on the substituent X, with those of 1d being the most substantial. The 1,3,4-oxadiazole O or N atom and pyridine N atom were identified as metal-chelating sites. The fluorescence responses of 1d upon metal chelation were employed for developing truth tables for OR, NOR, INHIBIT, and EnNOR logic gates as well as "ON-OFF-ON" and "OFF-ONOFF" fluorescent switches in a single 1,3,4-oxadiazole molecular system.
- Li, Ai-Fang,Ruan, Yi-Bin,Jiang, Qian-Qian,He, Wen-Bin,Jiang, Yun-Bao
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experimental part
p. 5794 - 5802
(2010/08/19)
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- Investigation of interaction of benzoquinones and naphthoquinones with substituted hydrazides
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(Chemical Equation Presented) Nucleophilic attack by substituted hydrazides on C-2, C-3 of 2,3,5,6-tetrachloro-1,4-benzoquinone and 2,3-dichloro-1,4- naphthoquinone initiates the formation of benzo[e][1,3,4]oxadiazine and benzo- as well as naphthoxadiazepine derivatives. On the other hand, substituted hydrazides attack 1,4-naphthoquinone-2,3-dicarbonitrile to form benzo[f]indazole-4,9-dione derivatives. A rationale for the conversions observed is presented.
- Hassan, Alaa A.,Ibrahim, Yusria R.,Shawky, Ahmed M.
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experimental part
p. 118 - 124
(2010/04/23)
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- Triazole Derivative, and Light-Emitting Element, Light-Emitting Device, and Electronic Device Using Triazole Derivative
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A novel triazole derivative which has a large energy gap and can be used for electron-transporting layer of a light-emitting element or as a host material. In addition, a light-emitting element which has higher emission efficiency by using the novel triazole derivative. Furthermore, a low power consumption light-emitting device and electronic device. A triazole derivative having a structure represented by the general formula (G1). In the formula, Py represents a pyridyl group. R11 and R12 each represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group.
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- Facile synthesis and stracture of novel 2,5-disubstituted 1,3,4-selenadiazoles
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The reaction of hydrazide with carbony] chloride in the presence of sodium carbonates leads to the corresponding 1,2- diacylhydrazines [1a-t, R 1C(O)NHNHC(O)R2, R1 = aryl, R2 = aryl or alkyl] in moderate to excellent yield (57-90%). The latter reacts with 2,4-diphenyl-l,3-diselenadiphosphetane- 2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2a-t, 51-99% yield). All compounds were characterized spectroscopically and six compounds were characterized crystalloqraphically. Wiley-VCH Verlag GmbH & Co. KGaA.
- Hua, Guoxiong,Li, Yang,Fuller, Amy L.,Slawin, Alexandra M.Z.,Woollins, J. Derek
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experimental part
p. 1612 - 1618
(2009/08/09)
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- TRIAZOLE DERIVATIVE, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, AND ELECTRONIC DEVICE
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A substance having high excitation energy is provided. In particular, a substance having high triplet excitation energy is provided. Further, a light-emitting element, a light-emitting device, and an electronic device each having high emission efficiency and low driving voltage are provided. A triazole derivative to which an amino group is bonded is provided. In addition, a light-emitting element, a light-emitting device, and an electronic device each including the triazole derivative to which the amino group is bonded are provided.
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Page/Page column 118
(2009/07/25)
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- Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities
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Substituted carboxylic acid hydrazides 1a-d reacted with ethenetetracarbonitril 2 in dimethyl formamide with the formation of diacylhydrazines 4a-d and 5-amino-1-substiuted pyrazole-3,3,4-tricarbonitriles 5a-d. On the other hand, 1a-d reacted with diethyl
- Abdel-Aziz, Mohamed,Abuo-Rahma, Gamal El-Din A.,Hassan, Alaa A.
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experimental part
p. 3480 - 3487
(2009/12/04)
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- Triazole Derivative, Light-Emitting Element, Light-Emitting Device, and Electronic Device
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A substance having high excitation energy is provided. In particular, a substance having high triplet excitation energy is provided. Further, a light-emitting element, a light-emitting device, and an electronic device each having high emission efficiency and low driving voltage are provided. A triazole derivative to which an amino group is bonded is provided. In addition, a light-emitting element, a light-emitting device, and an electronic device each including the triazole derivative to which the amino group is bonded are provided.
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- Kinetics and mechanism of oxidation of benzohydrazide by bromate catalyzed by vanadium(IV) in aqueous acidic medium
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The reaction between benzohydrazide and potassium bromate catalyzed by vanadium(IV) was studied under pseudo-first-order condition keeping large excess of hydrazide concentration over that of the oxidant. The initiation of the reaction occurs through oxidation of the catalyst vanadium(IV), VO2+, to vanadium(V), VO2+, which then reacts with hydrazide to give N,N′-diacylhydrazine and benzoic acid as the products. The order in [H+] is found to be two, and its effect is due to protonation and hydrolysis of oxidized form of the catalyst to form HVO3. The oxidized form of the catalyst, VO2+, forms a complex with the protonated hydrazide as evidenced by the occurrence of absorption maxima at 390 nm. The rate of the reaction remains unaffected by the increase in the ionic strength. The activation parameters were determined, and data support the mechanism. The detailed mechanism and the rate equation are proposed for the reaction.
- Shewale,Phadkule,Gokavi
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p. 151 - 159
(2008/09/16)
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- A ceric ammonium nitrate N-dearylation of N-p-anisylazoles applied to pyrazole, triazole, tetrazole, and pentazole rings: Release of parent azoles. Generation of unstable pentazole, HN5/N5-, in solution
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(Chemical Equation Presented) The reaction of cerium(IV) ammonium nitrate (CAN) with a range of N-(p-anisyl)azoles in acetonitrile or methanol solvents leads to N-dearylation releasing the parent NH-azole and p-benzoquinone in comparable yields. The scope and limitations of the reaction are explored. It was successful with 1-(p-anisyl)pyrazoles, 2-(p-anisyl)-1,2,3-triazoles, 2-(p-anisyl)-2H-tetrazoles, and 1-(p-anisyl)pentazole. The dearylation renders the p-anisyl group as a potentially useful N-protecting group in azole chemistry. The azole released in solution from 1-(p-anisyl)pentazole is unstable HN5, the long-sought parent pentazolic acid. p-Anisylpentazole samples were synthesized with combinations of one, two, and three 15N atoms at all positions of the pentazole ring. The unstable HN 5/N5- produced at -40°C did not build up in the solution but degraded to azide ion and nitrogen gas with a short lifetime. The 15N-labeling of the N3- ion obtained from all samples proved unequivocally that it came from the degradation of HN 5 (tautomeric forms) and/or its anion N5- in the solution.
- Butler, Richard N.,Hanniffy, John M.,Stephens, John C.,Burke, Luke A.
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p. 1354 - 1364
(2008/04/12)
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- Triazole derivative, and light-emitting device, and electronic device with the use of triazole derivative
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It is an object of the present invention to provide a novel triazole derivative. Further, it is another object of the present invention to provide a light-emitting element having high luminous efficiency with the use of the novel triazole derivative. Moreover, it is still another object of the present invention to provide a light-emitting device and electronic devices which have low power consumption. A light-emitting element having high luminous efficiency can be manufactured with the use of a triazole derivative which is a 1,2,4-triazole derivative, in which an aryl group or a heteroaryl group is bonded to each of 3-position, 4-position, and 5-position, and in which any one of the aryl group or heteroaryl group has a 9H-carbazol-9-yl group.
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Page/Page column 41
(2008/12/08)
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- Reactions of substituted carbohydrazides with electron-poor olefins
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Substituted carbohydrazides 1a-e reacted with ethenetetracarbonitrile (2) in dimethylformamide with formation of diacylhydrazines 4a-e and 5-amino-1-substiuted pyrazole-3,3,4-tricarbonitriles 5a-e. On the other hand, 1a-c reacted with diethyl (E)-2,3-dicy
- Hassan, Alaa A.,Ibrahim, Yusria R.,Shawky, Ahmed M.
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experimental part
p. 998 - 1004
(2009/03/11)
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- Chemistry of 2-ylidenefuran-3(2H)-ones: XIX. Reaction of 5-aryl-2(oxoylidene)furan-3(2H)-ones with carboxylic acid hydrazides
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2-[2-(4-Chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one and methyl (5-aryl-3-oxo-2,3-dihydrofuran-2-ylidene)acetates react with carboxylic acid hydrazides to give the corresponding 3-substituted 2-acyl-6-aryl-3-hydroxy-2,3- dihydropyridazin-4(1H)-ones. Specificities of the product structure are discussed.
- Koz'minykh,Goncharov,Koz'minykh
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p. 864 - 867
(2008/02/10)
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- Microwave-induced conversion of acid hydrazides to N,N′- diacylhydrazines in solvent-free conditions
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A new and efficient method of converting acid hydrazides 1 to the corresponding N,N′-diacylhydrazines 2 under microwave irradiation and in solvent-free conditions has been described. Copyright Taylor & Francis Group, LLC.
- Sailu,Komaraiah,Reddy
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p. 1907 - 1910
(2007/10/03)
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- Tuning the electrical and optical properties of dinuclear ruthenium complexes for near infrared optical sensing
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Redox-active dinuclear ruthenium complexes with various 1,2-dicarbonylhydrazido (DCH) ligands are designed and prepared to have intense absorption in the near-infrared region for potential optical sensing in aqueous media, as demonstrated for sensing hydrogen peroxide in this study.
- Xun, Shidi,LeClair, Gaetan,Zhang, Jidong,Chen, Xin,Gao, Jian Ping,Wang, Zhi Yuan
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p. 1697 - 1700
(2007/10/03)
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- 1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis
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Oxadiazoles were generated upon a dehydrative cyclization reaction with 2-acyl hydrazides bound to the polymeric support via one of their N atoms using TFAA as a dehydration agent.
- Cesarini, Sara,Colombo, Nicoletta,Pulici, Maurizio,Felder, Eduard R.,Brill, Wolfgang K.-D.
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p. 10223 - 10236
(2007/10/03)
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- A facile synthesis of acylhydrazines from acylbenzotriazoles
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Acylbenzotriazoles were found to react with substituted hydrazines and aqueous hydrazine under very mild conditions, thus affording a facile synthesis of three types of acylhydrazines in moderate to excellent yields.
- Wang, Xiaoxia,Yu, Hongping,Xu, Peifang,Zheng, Renwei
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p. 595 - 597
(2007/10/03)
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- Thiylation of functionalized electrophiles with sulfur in basic reductive systems
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Functionalized electrophiles, specifically acetyl chloride, benzoyl chloride, chloroacetylchloride, benzenesulfonyl chloride, and N,N,4-trichlorobenzenesulfonamide, were brought into reaction with sulfur in the systems hydrazine hydrate-NaOH and sodium sulfide-water-ethanol. The efficiencies of these systems were compared. The reaction of chloroacetyl chloride with sulfur in the system hydrazine hydrate-base afforded new types of polymeric compounds, poly[(diacylhydrazine)polysulfides]. The reaction mechanisms were discussed.
- Deryagina,Russavskaya,Grabel'nykh
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p. 346 - 349
(2007/10/03)
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- An Efficient Oxidation of Acid Hydrazides to N,N′-Diacylhydrazines Using Copper(II) Acetate in Solvent-Free Conditions Under Microwave Irradiation
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A simple and efficient method for solvent free "dry" state transformation of acid hydrazides 1 to corresponding N,N′ -diacylhydrazines 2 using copper(II) acetate under microwave irradiation has been described. The products are obtained in good yields and excellent purities.
- Mogilaiah,Prashanthi,Reddy, G. Randheer
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p. 3741 - 3745
(2007/10/03)
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- An expeditious and convenient one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles
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A convenient, one pot procedure is reported for the synthesis of a variety of 2,5-disubstituted-1,3,4-oxadiazoles by condensing monoarylhydrazides with acid chlorides in HMPA solvent under the microwave heating. The yields are good to excellent, the process is rapid and does not need any added acid catalyst or dehydrating reagent.
- Mashraqui, Sabir H.,Ghadigaonkar, Shailesh G.,Kenny, Rajesh S.
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p. 2541 - 2545
(2007/10/03)
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- Process for the preparation of symmetrical diacylhydrazines
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Process for the preparation of symmetrical diacylhydrazines having general formula (I): R1—CO—NH—NH—CO—R1wherein R1represents a linear or branched C1-C18alkyl group; a linear or branched C2-C8alkoxyalkyl group; a C2-C8cyanoalkyl group; a C5-C8cycloalkyl group, said cycloalkyl group optionally containing a heteroatom selected from oxygen, nitrogen and sulfur; a C6-C18aryl group; a C7C20arylalkyl group or alkylaryl group, said arylalkyl or alkylaryl groups optionally substituted with one or more hydroxyl groups, or with one or more linear or branched C1-C8alkoxyl groups; comprising: (a) reacting an ester of a carboxylic acid having general formula (II): R1—CO—OR2wherein R1has the same meanings defined above and R2represents a linear or branched C1-C18alkyl group, with hydrazine, in its pure or hydrated state, obtaining a monoacylhydrazine having general formula (III): R1—CO—NH—NH2; (b) reacting the monoacylhydrazine having general formula (III) obtained in step (a), with a β-ketoester having general formula (IV): R3—CO—CH2—COOR4wherein R3represents a linear or branched C1-C18alkyl group, or a C6-C18aryl group and R4represents a linear or branched C1-C18alkyl group, obtaining the desired symmetrical diacylhydrazine having general formula (I).
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- A simple and efficient oxidation of hydrazides to N,N'-diacylhydrazines using Oxone in an aqueous medium
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Substituted aromatic hydrazides have been oxidised to N,N'- diacylhydrazines in high yields using Oxone in an aqueous medium at room temperature.
- Kulkarni,Kadam,Desai, Uday V.,Mane,Wadgaonkar
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p. 184 - 185
(2007/10/03)
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- An alternative channel of reductive condensation of trichloromethylarenes with hydrazines
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The reductive condensation of trichloromethylarenes with hydrazines can proceed without intermediate formation of pyridinium salts and without participation of pyridine in the reduction act. Variants of reductive condensation using hydrazines as reducting agents and α-chlorobenzylhydrazines and hydrazonoyl chlorides, nitrite imines, or hydrazonoylpyridinium salts as intermediates are considered. α-Chlorobenzylhydrazines and hydrazonoyl chlorides are shown to be the most probable intermediates.
- Belen'kii,Luiksaar,Chuvylkin,Krayushkin
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p. 886 - 893
(2007/10/03)
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- Some hypervalent iodine(III) mediated solid-state transformations
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Some known hypervalent iodine(III) mediated reactions, viz (i) dimerization of acid hydrazides 1a-i, (ii) α-tosyloxylation of acetophenones 3a-f, and (iii) α-hydroxylation of acetophenones 3c,d,f have been effected in solid-state.
- Prakash, Om,Sharma, Vijay
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p. 229 - 231
(2007/10/03)
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- Syntheses of hydrazides by a direct condensation reaction using phosphorous acid-iodine as a reagent
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Aliphatic and aromatic hydrazides have been prepared in high to moderate yields by a direct condensation reaction of aliphatic or aromatic carboxylic acids with hydrazine or phenylhydrazine using phosphorous acid-iodine as reagent and pyridine as base and solvent. With aliphatic carboxylic acids, we obtained good results heating at 80-90°, for 5-6 hours, but with aromatic carboxylic acids are necessary 140-150°, for the same period of time.
- Chiriac, Constantin I.,Onciu, Mǎrioara,Tru?can, Ion,Tǎnasǎ, Mihaela Fulga,Bǎdǎrǎu, Cristina
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p. 143 - 146
(2007/10/03)
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