- Synthesis of 1H-indazole: A combination of experimental and theoretical studies
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A new practical synthesis of 1H-indazole is presented. A previous mechanism for the cyclization step is proved to be nonfeasible and a hydrogen bond propelled mechanism is proposed. The new mechanism is suitable for similar cyclization, and a new reaction is predicted. Springer Science+Business Media B.V. 2012.
- Chen, Xinzhi,Zhou, Shaodong,Qian, Chao,He, Chaohong
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Read Online
- A novel potent metal-binding NDM-1 inhibitor was identified by fragment virtual, SPR and NMR screening
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NDM-1 can hydrolyze nearly all available β-lactam antibiotics, including carbapenems. NDM-1 producing bacterial strains are worldwide threats. It is still very challenging to find a potent NDM-1 inhibitor for clinical use. In our study, we used a metal-binding pharmacophore (MBP) enriched virtual fragment library to screen NDM-1 hits. SPR screening helped to verify the MBP virtual hits and identified a new NDM-1 binder and weak inhibitor A1. A solution NMR study of 15N-labeled NDM-1 showed that A1 disturbed all three residues coordinating the second zinc ion (Zn2) in the active pocket of NDM-1. The perturbation only happened in the presence of zinc ion, indicating that A1 bound to Zn2. Based on the scaffold of A1, we designed and synthesized a series of NDM-1 inhibitors. Several compounds showed synergistic antibacterial activity with meropenem against NDM-1 producing K. pneumoniae.
- Bai, Weiqi,Cheng, Kai,Gao, Yan,Guo, Huifang,He, Wei,Li, Conggang,Li, Zhuorong,Wu, Cai
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- Indole-3-carbinol and 1,3,4-oxadiazole hybrids: Synthesis and study of anti-proliferative and anti-microbial activity
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In the present study, molecular hybrids of indole-3-carbinol and 1,3,4-oxadiazole-2-thiols have been designed and synthesized. The thiol analogues consisted of diversely substituted benzyl and alkyl groups with different electronic properties. The structures of all the newly synthesized scaffolds and target compounds were ascertained using 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. All the final compounds were screened in vitro for their anti-proliferative and anti-microbial activity. Three compounds showed excellent anti-proliferative activity with more than 70% cell growth inhibition against three cancer cell lines, HepG2 (human liver hepatocellular carcinoma), HeLa (human cervix carcinoma), and MCF-7 (human breast carcinoma). In the anti-microbial studies, compounds with electron-withdrawing fluoro or nitro substituent displayed appreciable activity similar to that of standard drugs. Also, the final compounds are non-toxic to non-cancerous Vero cell line.
- Gokhale, Nikhila,Panathur, Naveen,Dalimba, Udayakumar,Kumsi, Manjunatha
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- Hydrolysis mechanisms for the acetylpyridinephenylhydrazone ligand in sulfuric acid
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The excess acidity method was applied to rate data obtained for 2-acetylpyridinephenylhydrazone hydrolysis in strong acid media using various aqueous/organic solvents, and it was observed that the reaction rate decreases with increasing permittivity of the medium. Two hydrolysis mechanisms are indicated. Below 0.6 M H2SO4, no hydrolysis was observed; between 0.6 and 6.0 M H2SO4, the substrate hydrolyzes by an A-SE2 mechanism and switches to an A-2 mechanism at higher acidity. This change of mechanism was justified on the basis of the syn and anti rotational conformers of the diene -N(1)D=C-C=N(2)- group; the greater stability of the former can be explained by the formation of hydrogen bonds between the proton and the N(1) and N(2) nitrogen atoms, giving rise to a very stable five-membered ring. If the syn conformer is predominant, then no hydrolysis is observed; above 0.6 M, the attack of a second proton gives rise to a balance between the syn and anti forms, the latter being responsible for the hydrolysis of the hydrazone group.
- Garcia, Begona,Munoz, Maria S.,Ibeas, Saturnino,Leal, Jose M.
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- Synthesis and Characterization of Telmisartan-Derived Cell Death Modulators to Circumvent Imatinib Resistance in Chronic Myeloid Leukemia
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New strategies to eradicate cancer stem cells in chronic myeloid leukemia (CML) include a combination of imatinib with peroxisome proliferator-activated receptor gamma (PPARγ) ligands. Recently, we identified the partial PPARγ agonist telmisartan as effective sensitizer of resistant K562 CML cells to imatinib treatment. Here, the importance of the heterocyclic core on the cell death-modulating effects of the telmisartan-derived lead 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid (3 b) was investigated. Inspired by the pharmacodynamics of HYL-6d and the selective PPARγ ligand VSP-51, the benzimidazole was replaced by a carbazole or an indole core. The results indicate no correlation between PPARγ activation and sensitization of resistant CML cells to imatinib. The 2-COOH derivatives of the carbazoles or indoles achieved low activity at PPARγ, while the benzimidazoles showed 60-100 % activation. Among the 2-CO2CH3 derivatives, only the ester of the lead (2 b) slightly activated PPARγ. Sensitizing effects were further observed for this non-cytotoxic 2 b (80 % cell death), and to a lesser extent for the lead 3 b or the 5-Br-substituted ester of the benzimidazoles (5 b).
- Schoepf, Anna M.,Salcher, Stefan,Hohn, Verena,Veider, Florina,Obexer, Petra,Gust, Ronald
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- Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine
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Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.
- Borate, Kailaskumar,Choi, Kyoungmin,Goetz, Roland,Hartwig, John F.,Shinde, Harish,Wang, Justin Y.,Zuend, Stephan J.
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supporting information
p. 399 - 408
(2020/10/29)
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- Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine
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In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.
- Hosseini-Sarvari, Mona,Koohgard, Mehdi
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supporting information
p. 5905 - 5911
(2021/07/12)
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- Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
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Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.
- Gou, Kun,Luo, Youfu,Luo, Yuan,Sun, Qingxiang,Tan, Yuping,Tao, Lei,Zhao, Yinglan,Zhou, Xia,Zhou, Yue,Zuo, Zeping
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- Synthesis and biological activity of conformationally restricted indole-based inhibitors of neurotropic alphavirus replication: Generation of a three-dimensional pharmacophore
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We have previously reported the development of indole-based CNS-active antivirals for the treatment of neurotropic alphavirus infection, but further optimization is impeded by a lack of knowledge of the molecular target and binding site. Herein we describe the design, synthesis and evaluation of a series of conformationally restricted analogues with the dual objectives of improving potency/selectivity and identifying the most bioactive conformation. Although this campaign was only modestly successful at improving potency, the sharply defined SAR of the rigid analogs enabled the definition of a three-dimensional pharmacophore, which we believe will be of value in further analog design and virtual screening for alternative antiviral leads.
- Barraza, Scott J.,Sindac, Janice A.,Dobry, Craig J.,Delekta, Philip C.,Lee, Pil H.,Miller, David J.,Larsen, Scott D.
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supporting information
(2021/06/18)
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- Synthesis of and characterization of some Heterocyclic Compounds derived from Thiophenol
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This research work involved preparation of heterogeneous pent lateral cyclic compounds (thiazolidine -4- one, benzothiazole, triazole, 4-oxothiazolidin) using thiophenol as raw materials: Thiophenol was reacted with mono chloroacetic acid in the presence of potassium hydroxide to prepare (sh1) followed by ortho amino aniline results the (sh2). The reaction of thiophenol with ethylchloroacetate afforded (sh3) and the reaction of (sh3) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4- triazole (sh5). A treatment of thiophenol with hydrazine hydrate to obtain the intermediate (sh6) with aromatic aldehyde synthesized azomethines (sh7- sh9) then treated with mercaptoacetic acid to obtained (sh10-sh12). A treatment of thiophenol with chloroacetyl chloride produced (sh13) compound then treated with hydrazine hydrate to obtain (sh14) compound followed by bromobenzaldehyde synthesized azomethine (sh15) compound then treated with mercaptoacetic acid to obtained (sh16) compound. Characterization results for the prepared compounds using IR spectroscopy, NMR and melting points confirmed their chemical structures.
- AL-Khazraji, Shaima Ibraheem Chyad
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p. 5655 - 5662
(2021/09/11)
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- 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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- PROCESS FOR THE SYNTHESIS OF ARYL HYDRAZINES
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The invention relates to a process for the synthesis of aryl hydrazinesof formula I or a salt thereof, which process comprises subjecting an arene of formula II to a coupling reaction with hydrazine or a derivative thereof, wherein the coupling reaction is conducted in the presence of a catalyst comprising palladium and a diphosphine ligand, wherein the phosphorus atoms are connected through two, three, four, or five atoms selected from car- bon, nitrogen, oxygen or iron, and in which the non-connecting phosphorus substituents are C1- C 10-alkyl or C3-C10-cycloalkyl, wherein the amount of Pd used is up to 0.5 mol-% relative to the amount of arene of formula II; and a base.
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Page/Page column 22; 25
(2020/06/01)
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- Synthesis method of oxalyl hydrazine ligands and application of oxalyl hydrazine ligands in C-N bond coupling reaction
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The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a synthesis method of oxalyl hydrazine ligands and application of the oxalyl hydrazine ligands to C-N coupling reaction. The invention provides a method for synthesizing oxalyl hydrazine ligands by taking hydrazine compounds and oxalyl chloride as raw materials. The method has the advantages that the raw materials are easy to obtain, the operation is simple, the post-treatment is easy, and the method is suitable for industrial large-scale production; furthermore, coupling of aryl iodide andhydrazine hydrate is realized by utilizing oxalyl hydrazine ligands, and aryl hydrazine is synthesized. The method is mild in reaction condition, safe, efficient and suitable for industrial production.
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Paragraph 0020; 0024-0026
(2020/11/02)
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- Synthetic method ofphenylhydrazine
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The invention discloses a synthetic method of phenylhydrazine. Aniline, hydrochloric acid, sodium nitrite, water, an ammonium bisulfite solution, 98% sulfuric acid, caustic soda liquid and caustic soda flakes are adopted as main raw materials, aniline, hydrochloric acid, sodium nitrite and tap water are converged through a metering pump and a flowmeter respectively and then pass through a tubularreactor (a miller-grid tube reactor) at a high speed to be subjected to diazotization reaction and diazonium salt liquid is obtained. The diazonium salt solution subjected to the pipeline reaction flows into a reduction tank to be subjected to a cold reduction reaction with an ammonium bisulfite solution, and heating is performed to perform a thermal reduction reaction. Concentrated sulfuric acidis added into the reduction solution and heated for hydrolysis. The hydrolysate is cooled and then filter pressing operation is performed, solid crystals are obtained after filtering, caustic soda liquid is added for dissolving and then caustic soda flakes are added for neutralizing. Pressure filtration is performed to remove salt and the filtrate stands for layering to obtain an oil phase which is the phenylhydrazine finished product.
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Paragraph 0023-0058
(2020/04/06)
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- Deciphering the robustness of pyrazolo-pyridine carboxylate core structure-based compounds for inhibiting α-synuclein in transgenic C. elegans model of Synucleinopathy
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Parkinson's disease (PD), a calamitous neurodegenerative disorder with no cure till date, is closely allied with the misfolding and aggregation of α-Synuclein (α -Syn). Inhibition of α-Syn aggregation is one of the optimistic approaches for the treatment for PD. Here, we carried out hypothesis-driven studies towards synthesising a series of pyrazolo-pyridine carboxylate containing compounds (7a–7m) targeted at reducing deleterious α-Syn aggregation. The target compounds were synthesized through multi-step organic synthesis reactions. From docking studies, compounds 7b, 7g and 7i displayed better interaction with the key residues of α-Syn with values: ?6.8, ?8.9 and ?7.2 Kcal/mol, respectively. In vivo transgenic C. elegans model of Synucleinopathy was used to evaluate the ability of the designed and synthesized compounds to inhibit α-Syn aggregation. These lead compounds 7b, 7g and 7i displayed 1.7, 2.4 and 1.5-fold inhibition of α-Syn with respect to the control. Further, the strategy of employing pyrazolo-pyridine-based compounds worked with success and these scaffolds could be further modified and validated for betterment of endpoints associated with PD.
- Hoda, Nasimul,Maqbool, Mudasir,Rajvansh, Roshani,Srividya, Kottapalli
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- Preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one
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The invention provides a preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one. The method comprises the steps: taking aniline as a raw material; reducing witha catalyst X to prepare phenylhydrazine; under the action of acetaldehyde and sodium cyanate, carrying out cyclization on phenylhydrazine to generate 1-phenyl-3-methyl-1H-1,2,4-triazole-5-one; carrying out a reaction on 1-phenyl-3-methyl-1H-1,2,4-triazole-5-one and monochlorodifluoromethane under the action of a catalyst Y to generate 1-phenyl-3-methyl-4-difluoromethyl-1H-1,2,4-triazole-5-one, and carrying out catalytic chlorination through a catalyst Z to prepare 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one.
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Paragraph 0032-0033; 0038; 0040; 0043
(2020/10/04)
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- Phenylhydrazine compound clean production method
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The invention discloses a phenylhydrazine compound clean production method which comprises the steps of diazotization, reduction, acid precipitation, alkaline hydrolysis and separation, and acid adopted in the diazotization step is sulfuric acid; acid adopted in the acid precipitation step is sulfuric acid; alkali adopted in the alkaline hydrolysis step is soda ash. Sulfuric acid is used for replacing hydrochloric acid, hydrochloric acid volatilization is prevented from polluting the environment, only one salt of sodium sulfate exists in the mother liquor, even if a small amount of sodium sulfite exists, air can be introduced to oxidize the sodium sulfite into sodium sulfate, then the qualified industrial product anhydrous sodium sulfate is obtained through distillation dehydration, centrifugation and high-temperature oxidation, and considerable economic benefits are achieved; distillation effluent is reused for production, and no waste water is generated.
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Paragraph 0031-0042
(2020/09/23)
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- One-Pot Synthesis of Indoles and Pyrazoles via Pd-Catalyzed Couplings/Cyclizations Enabled by Aqueous Micellar Catalysis
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An effective one-pot synthesis of either indoles or pyrazoles can be achieved via Pd-catalyzed aminations followed by subsequent cyclizations facilitated by aqueous micellar catalysis. This new technology includes efficient couplings with low loadings of palladium, a more stable source of the required hydrazine moiety, greater atom economy for the initial coupling, and reduced reaction temperatures, all leading to environmentally responsible processes.
- Akporji, Nnamdi,Braga, Felipe C.,Gabriel, Christopher M.,Landstrom, Evan B.,Lee, Nicholas R.,Lipshutz, Bruce H.
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supporting information
(2020/09/02)
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- Method for synthesis of phenylhydrazine from diazonium salt
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The invention provides a method for synthesis of phenylhydrazine from a diazonium salt. The method includes: A) diazotizing aniline to obtain diazobenzene; B) carrying out reduction reaction on diazobenzene and organophosphorus to obtain a first intermediate; and C) subjecting the first intermediate to heating reflux acidification reaction in the presence of an organic solvent and acid to obtain phenylhydrazine. The method provided by the invention adopts electron-rich organphosphorus as the reducing agent to reduce the diazonium salt, and has the advantages of no generation of salt wastewater and recycling of unreacted organophosphorus and oxidized organophosphorus into products with economic benefits. The synthesis of phenylhydrazine needs three steps in total, thus simplifying the complex operation procedure in industry. To sum up, compared with the prior art, the method provided by the invention has better industrialization application prospects.
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- Azologization of serotonin 5-HT3 receptor antagonists
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The serotonin 5-hydroxytryptamine 3 receptor (5-HT3R) plays a unique role within the seven classes of the serotonin receptor family, as it represents the only ionotropic receptor, while the other six members are G protein-coupled receptors (GPCRs). The 5-HT3 receptor is related to chemo-/radiotherapy provoked emesis and dysfunction leads to neurodevelopmental disorders and psychopathologies. Since the development of the first serotonin receptor antagonist in the early 1990s, the range of highly selective and potent drugs expanded based on various chemical structures. Nevertheless, on-off-targeting of a pharmacophore’s activity with high spatiotemporal resolution as provided by photopharmacology remains an unsolved challenge bearing additionally the opportunity for detailed receptor examination. In the presented work, we summarize the synthesis, photochromic properties and in vitro characterization of azobenzene-based photochromic derivatives of published 5-HT3R antagonists. Despite reported proof of principle of direct azologization, only one of the investigated derivatives showed antagonistic activity lacking isomer specificity.
- Rustler, Karin,Maleeva, Galyna,Bregestovski, Piotr,K?nig, Burkhard
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p. 780 - 788
(2019/04/17)
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- Pyrazolo pyrimidine derivative and its preparation method and application (by machine translation)
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The invention discloses a pyrazolo pyrimidine ketone derivatives, wherein R1 For nicotinic acid, isonicotinic acid, 2 - chloro nicotinic acid, 6 - chloro nicotinic acid, 2 - bromo nicotinic acid, 6 - bromo nicotinic acid, 2 - fluoro nicotinic acid, 6 - fluoro nicotinic acid, 6 - methoxy nicotinic acid or 2 - methoxy nicotinic acid; R2 Hydrogen, fluoro, chloro or methyl; R3 Is hydrogen or methyl. Also disclosed the preparation method of the derivative and application, by chemical synthetic way to synthesize 40 for the purpose of the compound, and further by the introduction of the the purpose of the chiral compound to the secondary structure is optimized, so that the preparation of the pyrazole and pyrimidinone derivatives with broad-spectrum of cooperativity antifungal activity, in particular to the apple rot bacteria and germ inhibiting activity represent significant; the application in order to develop pyrazolo pyrimidine compound derivatives as the active ingredient to provide the basis for a novel bactericide. (by machine translation)
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Paragraph 0042; 0043; 0044; 0045
(2019/10/23)
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- Synthetic method of phenylhydrazine
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The invention relates to a synthetic method of phenylhydrazine. The method comprises the steps of with phenol and hydrazine hydrate as raw materials, carrying out a reaction with a CuO/Al2O3 compositecatalyst at a certain temperature to synthesize phenylhydrazine; hydrazine hydrate maintains excessive in the reaction system to make the reaction of phenol complete, and water produced in the reaction is continuously separated and removed in the reaction process; after the reaction is finished, the hydrazine hydrate is recovered by reduced pressure distillation, the remaining liquid has the catalyst separated and is washed by a sodium carbonate solution and pure water, and then the finished product of phenylhydrazine is obtained. Compared with a traditional diazotization reaction process forsynthesis of phenylhydrazine, the method provided by the invention has the advantages of mild reaction conditions, fewer reaction steps, simple operation, fewer by-products and wastes, and low energyconsumption; the yield is 90% or more, the catalyst can be recycled, the production cost is low, and the method is a new energy-saving and environmental-protection technology.
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Paragraph 0009
(2018/05/07)
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- Method for synthesizing phenylhydrazine
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The invention relates to a method for synthesizing phenylhydrazine. The method comprises the following step: performing reaction on phenol and hydrazine hydrate which serve as raw materials by using sodium tripolyphosphate serving as a catalyst at certain temperature to synthesize the phenylhydrazine. In a reaction system, the amount of the hydrazine hydrate keeps excessive, so that the phenol canbe reacted completely; in a reaction process, water generated by the reaction is continuously separated and removed; after the reaction is ended, reduced pressure distillation is performed to recyclethe hydrazine hydrate; after remaining liquid is washed with a sodium carbonate solution and pure water through a separation catalyst, a phenylhydrazine finished product is obtained. Compared with aconventional diazo-reaction process for synthesizing the phenylhydrazine, the method is mild in reaction condition and easy to operate; the number of reaction steps is small, and the number of byproducts and wastes is small; the energy consumption is low, and the yield is 90 percent or above; the catalyst can be recycled, so that the production cost is low; the method is an energy-saving and environmentally-friendly novel process.
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Paragraph 0009-0011
(2018/06/26)
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- A process for preparing phenyl hydrazine method (by machine translation)
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The invention relates to a process for preparing arylhydrazines of the method, the method is to phenol and hydrazine as raw material, for sodium hexametaphosphate as the catalyst for reaction at certain temperature preparation phenyl hydrazine, hydrazine hydrate in the reaction system to maintain excess, in order to make the phenol reaction is complete, the reaction process is constantly in the reaction separated from the generated water removing, after the reaction is distilled under reduced pressure recovery hydrazine hydrate, the remaining liquid is separated catalyst, for sodium carbonate solution and pure water obtained after arylhydrazines finished product. With the traditional diazotization reaction process compared with the synthesis of phenyl hydrazine, the invention mild reaction conditions, few reaction steps, the operation is simple, and less waste by-product, low energy consumption, and the yield is 90% or more, the catalyst can be recycled, the production cost is low, it is a kind of energy saving and environment protecting the new process. (by machine translation)
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Paragraph 0009-0011
(2018/06/26)
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- Method for preparing phenylhydrazine
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The invention discloses a method for preparing phenylhydrazine. The method uses phenol and hydrazine hydrate as raw materials, and uses HD-8 macroporous strong acid cation exchange resin as a catalyst, a reaction is performed at a certain temperature to prepare the phenylhydrazine, the hydrated hydrazine is kept excess in the reaction system to make the phenol reacted fully, water formed by the reaction is continuously separated and removed in the reaction process, after the reaction is completed, reduced-pressure distillation is performed to recover the hydrazine hydrate, the catalyst is recovered, the remaining liquid is washed by using a sodium carbonate solution and pure water, and therefore a finished product of the phenylhydrazine is obtained. Compared with a traditional diazotization reaction process for synthesizing the phenylhydrazine, the method provided by the invention has mild reaction conditions, less reaction steps, simple operation, less by-products and waste and low energy consumption, the yield is 90% or more, the catalyst can be recycled, the production costs are low, and the method is a novel energy-saving environmentally-friendly process.
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Paragraph 0007; 0008; 0009-0011
(2018/07/30)
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- Direct Catalytic Hydrogenation of Simple Amides: A Highly Efficient Approach from Amides to Amines and Alcohols
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A highly chemoselective and reactive direct catalytic reduction of various amides to amines and alcohols was developed by using a tetradentate ruthenium complex. The catalytic system showed excellent activity (turnover numbers up to 19 600) and great functional group tolerance under mild reaction conditions, compared to several bidentate and tridentate ruthenium-catalyzed systems.
- Shi, Liyang,Tan, Xuefeng,Long, Jiao,Xiong, Xiong,Yang, Song,Xue, Peng,Lv, Hui,Zhang, Xumu
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supporting information
p. 546 - 548
(2017/01/18)
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- A phenyl hydrazine preparation method (by machine translation)
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The invention discloses a phenyl hydrazine preparation method, the method is a chloramine is reacted with aniline for preparing phenyl hydrazine hydrochloride, then the phenyl hydrazine hydrochloride in the lye and get the arylhydrazines. With the traditional diazotization reaction process for preparing arylhydrazines compared with the method of, the invention adopts the method of the mild reaction conditions, few reaction steps, the operation is simple, few by-products, low energy consumption, high yield, little consumption of raw materials, the production cost is low, it is a kind of energy saving and environment protecting the new process. (by machine translation)
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Paragraph 0008; 0009; 0010
(2017/08/30)
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- Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid
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N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone.
- Maclean, Mark A.,Diez-Cecilia, Elena,Lavery, Christopher B.,Reed, Mark A.,Wang, Yanfei,Weaver, Donald F.,Stradiotto, Mark
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supporting information
p. 100 - 104
(2015/12/18)
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- Synthetic method of phenylhydrazine hydrochloride
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The invention discloses a method for synthesizing phenylhydrazine hydrochloride through catalytic hydrogenation. The method is characterized in that benzene diazonium chloride and a hydrogenation catalyst are contacted in the presence of hydrogen and the phenylhydrazine hydrochloride is prepared. With the adoption of the method, the solid catalytic hydrogenation catalyst is used, the reaction process is simplified, and the economy is substantially improved; meanwhile, the catalytic hydrogenation method is adopted, production of sulfur dioxide is avoided, the method is environment-friendly, less salt wastewater is produced and comprises the single component, and recovery and treatment are facilitated.
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Paragraph 0045; 0046; 0047
(2016/10/31)
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- Phenyl hydrazine synthesis method
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The invention discloses a synthetic method of phenylhydrazine. The synthetic method comprises the following steps: adding dilute sulfuric acid into aniline, dropwise adding ammonium nitrite at 0-5 DEG C, and then performing thermal reaction for 4-6 minutes; then cooling to a temperature between -5 and -10 DEG C, adding a solid reducing agent, and stirring violently; when the temperature of the reaction system naturally rises to be more than 40 DEG C, adding dilute sulfuric acid to adjust the pH value to be 2-4, and heating to 70-100 DEG C to react for 4-6 hours; and separating the obtained reaction product to obtain phenylhydrazine. According to the synthetic process of phenylhydrazine, disclosed by the invention, aniline is used as a raw material, dilute sulfuric acid is used as salt forming and acidifying reagents, ammonium nitrite is used as a diazotization reagent, ammonium sulfite and/or ammonium hydrogen sulfite is used as the reducing agent, ammonia gas is used for neutralizing a reaction solution, phenylhydrazine is finally obtained by virtue of extraction and distillation, and a byproduct salt is single ammonium sulfate.
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Paragraph 0031; 0032; 0033; 0034; 0035
(2017/06/02)
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- Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors
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Six series of novel 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives conjugated with aza-aryl formamide/amine scaffords were designed and synthesized through a structure-based molecular hybridization approach. The target compounds were evaluated for c-Met kinase inhibitory activities and cytotoxicity against four cancer cell lines (HT-29, A549, MKN-45 and MDA-MB-231) in vitro. Most compounds exhibited moderate to excellent potency, and the most promising candidate 26c (c-Met kinase IC50 = 8.2 nM) showed a 4.7-fold increase in cytotoxicity against c-Met-addicted MKN-45 cell line in vitro (IC50 = 3 nM), superior to that of Foretinib (IC50 = 23 nM). The preliminary structure-activity relationship indicated that a 1H-benzo [e] [1,3,4]thiadiazine-3-carboxamide-4,4-dioxide moiety as linker contributed to the antitumor potency.
- Zhao, Sijia,Zhang, Yu,Zhou, Hongyang,Xi, Shuancheng,Zou, Bin,Bao, Guanglong,Wang, Limei,Wang, Jiao,Zeng, Tianfang,Gong, Ping,Zhai, Xin
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- Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi
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A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.
- Wang, Xing,Chen, Yong-Fei,Yan, Wei,Cao, Ling-Ling,Ye, Yong-Hao
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- ORGANIC COMPOUND, COMPOSITION, ORGANIC OPTOELECTRIC DEVICE, AND DISPLAY DEVICE
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An organic compound, a composition for an organic optoelectric device, and a display device, the compound being represented by the following Chemical Formula 1:
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- Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs
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A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.
- Nakao, Syuhei,Mabuchi, Miyuki,Shimizu, Tadashi,Itoh, Yoshihiro,Takeuchi, Yuko,Ueda, Masahiro,Mizuno, Hiroaki,Shigi, Naoko,Ohshio, Ikumi,Jinguji, Kentaro,Ueda, Yuko,Yamamoto, Masatatsu,Furukawa, Tatsuhiko,Aoki, Shunji,Tsujikawa, Kazutake,Tanaka, Akito
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supporting information
p. 1071 - 1074
(2014/03/21)
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- Facile and convenient synthesis of aryl hydrazines via copper-catalyzed C-N cross-coupling of aryl halides and hydrazine hydrate
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An efficient and convenient method for the synthesis of aryl hydrazines has been developed via copper-catalyzed cross-coupling of aryl bromides and hydrazine with a readily accessible ligand and water as a solvent. The multigram scale procedure is applicable to aryl bromides bearing both moderately electron-donating and electron-withdrawing substituents in the aromatic nucleus. No column chromatography is required to obtain aryl hydrazine hydrochlorides in good yields.
- Kurandina, Daria V.,Eliseenkov, Eugene V.,Ilyin, Petr V.,Boyarskiy, Vadim P.
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p. 4043 - 4048
(2014/06/09)
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- Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
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Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.
- Neumann, Donna M.,Cammarata, Amy,Backes, Gregory,Palmer, Glen E.,Jursic, Branko S.
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p. 813 - 826
(2014/01/23)
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- Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives
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Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl) ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3- triazol-4-yl)-4,9-dihydro-3H-β-carbolines that can be transformed into β-carboline and tetrahydro-β-carboline derivatives.
- Pohodylo,Matiichuk,Obushak
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p. 275 - 279
(2014/04/17)
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- Base-induced dehydrogenation of ruthenium hydrazine complexes
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Treatment of [RuCl(PP3iPr)]+Cl- (PP3iPr = P(CH2CH2P iPr2)3) with hydrazine, phenylhydrazine, and methylhydrazine afforded side-on bound hydrazine complexes [RuCl(η 2-H2N-NH2)(η3-PP 3iPr)]+, [RuCl(η2-H 2N-NHPh)(η3-PP3iPr)] +, and [RuCl(η2-H2N-NHMe) (η3-PP3iPr)]+. The analogous reactions of [RuCl2(PP3Ph)] (PP 3Ph = P(CH2CH2PPh2) 3) with hydrazine, phenylhydrazine, and methylhydrazine afforded end-on bound hydrazine complexes [RuCl(η1-H2N-NH 2)(PP3Ph)]+, [RuCl(η 1-H2N-NHPh)(PP3Ph)]+, and [RuCl(η1-H2N-NHMe)(PP3Ph)] +. Treatment of parent hydrazine complex [RuCl(N2H 4)(PP3iPr)]+ with strong base afforded the dinitrogen and dihydride complexes [Ru(N2)(PP 3iPr)] and [RuH2(PP3 iPr)]. Treatment of phenylhydrazine complex [RuCl(NH 2NHPh)(PP3iPr)]+ with strong base afforded the hydrido ruthenaindazole complex [RuH(η2-NHi? - ?NC6H4)(η3-PP3iPr)] while similar treatment of methylhydrazine complex [RuCl(NH2NHMe) (PP3iPr)]+ afforded the hydrido methylenehydrazide complex [RuH(NHNi? - ?CH2)(PP 3iPr)]. Treatment of the hydrazine complexes [RuCl(NH 2NHR)(PP3Ph)]+ (R = H, Ph, Me) with strong base afforded the dinitrogen complex [Ru(N2)(PP 3Ph)].
- Field, Leslie D.,Li, Hsiu L.,Dalgarno, Scott J.,McIntosh, Ruaraidh D.
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p. 1570 - 1583
(2013/04/10)
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- Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400
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An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.
- Chen, Junmin,Zhang, Yimin,Hao, Wenyan,Zhang, Rongli,Yi, Fei
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p. 613 - 617
(2013/07/25)
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- Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition
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In our pursuit to develop new potential anticancer leads, we designed a combination of structural units of indole and substituted triazole; and a library of 1-{1-methyl-2-[4-phenyl-5-(propan-2-ylsulfanyl)-4H-1,2,4-triazol-3- yl]-1H-indol-3-yl}methanamine derivatives was synthesized and characterized. Cytotoxic evaluations of these molecules over a panel of three human cancer cell lines were carried out. Few molecules exhibited potent growth inhibitory action against the treated cancer cell lines at lower micro molar concentration. An in vitro assay investigation of these active compounds using recombinant human SIRT1 enzyme showed that one of the compounds (IT-14) inhibited the deacetylation activity of the enzyme. The in vivo study of IT-14 exemplified its promising action by reducing the prostate weight to the body weight ratio in prostate hyperplasia animal models. A remarkable decrease in the disruption of histoarchitecture of the prostate tissues isolated from IT-14 treated animal compared to that of the positive control was observed. The molecular interactions with SIRT1 enzyme were also supported by molecular docking simulations. Hence this compound can act as a lead molecule to treat prostatic hyperplasia.
- Panathur, Naveen,Dalimba, Udayakumar,Koushik, Pulla Venkat,Alvala, Mallika,Yogeeswari, Perumal,Sriram, Dharmarajan,Kumar, Vijith
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p. 125 - 138
(2013/10/01)
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- NOVEL COMPOUNDS FOR ORGANIC ELECTRONIC MATERIAL AND ORGANIC ELECTRONIC DEVICE USING THE SAME
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The present invention relates to novel compounds for organic electronic material, and organic electronic devices and organic solar cells using the same. The compounds for organic electronic material may be included in a hole transport layer, electron transport layer or hole injection layer, or may be used as host or dopant. With good luminous efficiency and excellent life property of the material, they may be used to manufacture OLEDs having very good operation life.
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- NOVEL ANTIVIRAL COMPOUNDS
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The present invention relates to a compound of formula I: or a pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification; a pharmaceutical composition comprising the same, a method for treating or preventing a viral infection such as HIV using the same.
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Page/Page column 84-85
(2012/05/31)
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- Configurational and constitutional information storage: Multiple dynamics in systems based on pyridyl and acyl hydrazones
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The C=N group of hydrazones can undergo E/Z isomerization both photochemically and thermally, allowing the generation of a closed process that can be tuned by either of these two physical stimuli. On the other hand, hydrazine-exchange reactions enable a constitutional change in a given hydrazone. The two classes of processes: 1) configurational (physically stimulated) and 2) constitutional (chemically stimulated) give access to short-term and long-term information storage, respectively. Such transformations are reported herein for two hydrazones (bis-pyridyl hydrazone and 2-pyridinecarboxaldehyde phenylhydrazone) that undergo a closed, chemically or physically driven process, and, in addition, can be locked or unlocked at will by metal-ion coordination or removal. These features also extend to acyl hydrazones derived from 2-pyridinecarboxaldehyde. Similarly to the terpydine-like hydrazones, such acyl hydrazones can undergo both constitutional and configurational changes, as well as metal-ion coordination. All these types of hydrazones represent dynamic systems capable of acting as multiple state molecular devices, in which the presence of coordination sites furthermore allows the metal ion-controlled locking and unlocking of the interconversion of the different states.
- Chaur, Manuel N.,Collado, Daniel,Lehn, Jean-Marie
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p. 248 - 258
(2011/03/21)
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- HETEROCYCLIC INHIBITORS OF AN Hh-SIGNAL CASCADE, MEDICINAL COMPOSITIONS BASED THEREON AND METHODS FOR TREATING DISEASES CAUSED BY THE ABERRANT ACTIVITY OF AN Hh-SIGNAL SYSTEM
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The invention relates to novel heterocyclic compounds and to the use thereof, to pharmaceutical compositions containing said chemical compounds as an active ingredient and to the use thereof for producing medicinal preparations for the human being and warm-blood animals for treating diseases caused by the aberrant activity of an Hedgehog (Hh)-signal system, in particular oncological diseases. The invention also relates to the use of the above-mentioned compounds in the form of ‘molecular pharmacological tools’ for examining (in vitro and in vivo) the biochemical features of the Hh-signal system, in particular, the interaction of Hh protein and transmembrane proteins, namely, suppressor Patched (Ptc) and protooncogenic proteins. The eight groups of the claimed compounds comprise the derivatives of 2,6-dihydro-7H-pyrazolo[3,4-d]pyridazine-7-one and 1,4-dihydropyrazolo[3,4-b][1,4]thiazine-5-one; N-acidylated 4-imidazo[1,2-a]pyrimidine-2-il-anilines; ([4H-thino[3,2-b]pyrrol-5-il) carbonyl]piperidine-4-carbonic acid amides; 2-(4carbomoilpyperidine-1-il)-isonicotinic acid amides; N-sylphonyl-1,2,3,4-tetrahydroquinoline-6-carbonic acid amides; and pyridine 2-amino-4,5,6,7-tetrahydrothieno[2,3-c] N-acidylated 3-azole derivatives.
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Page/Page column 20
(2011/04/14)
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- Synthesis and biological activity of pyrazolidine-3,5-dione substituted benzimidazole derivatives
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Condensation of o-phenylene diamine with chloro acetic acid gave 2-chloromethyl benzimdazole, which undergoes halide replacement with phenylhydrazines to give the corresponding N,N'-disubstituted hydrazines. Later these compounds were treated with diethyl malonate in presence of acetic acid to get the pyrazolidine-3,5-dione substituted benzimidazole derivatives. The synthesized compounds were subjected to microbiological screening and in vitro antiinflammatory activity.
- Tiwari, Abhishek,Tiwari, Varsha,Venkataramana,Madhavan
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experimental part
p. 1179 - 1182
(2012/01/05)
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- Palladium-catalyzed cross-coupling of aryl chlorides and tosylates with hydrazine
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Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross-coupling of aryl chlorides and tosylates with hydrazine. An appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4-toluenesulfonyl).
- Lundgren, Rylan J.,Stradiotto, Mark
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supporting information; experimental part
p. 8686 - 8690
(2011/01/08)
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- Synthesis, crystal structure, and fungicidal activity of novel 1,5-Diaryl-1H-pyrazol-3-oxyacetate derivatives
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A series of ethyl 2-(1,5-diaryl-1H-pyrazol-3-yloxy)acetate derivatives (5a-5i) have been efficiently synthesized by the reaction of 1,5-diaryl-1H-pyrazol-3-ols (4a-4i) with ethyl 2-bromoacetate. The structures of the newly synthesized compounds were characterized by 1H NMR spectra and elemental analysis, and the crystal structure of the compound ethyl 2-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yloxy)acetate (5c) was determined by single crystal X-ray diffraction analysis. The compound 5c belongs to triclinic system with space group P(-1), a = 5.8170(12) A, b = 11.804(2) A, c = 12.783(2) A, α = 83.89(2)°, β = 89.24(3)°, γ = 89.73(3)°, Formula weight: 356.80, Triclinic V = 872.7(3) A3, Dc = 1.358 mg/m3, Z = 2, F (000) = 372. Bioassay results indicated that the compound ethyl 2-(5-(4-fluorophenyl)-1- phenyl-1H-pyrazol-3-yloxy)acetate (5d) exhibited moderate inhibitory activity against Gibberella zeae at the dosage of 10 μg/mL.
- Liu, Yuanyuan,Shi, Hong,Li, Yufeng,Zhu, Hongjun
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scheme or table
p. 897 - 902
(2010/10/18)
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- Synthesis, anti-allergic, anti-asthmatic and anti-inflammatory activities of CEE-1 and CEE-2
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“Enhydrazone esters of formula (I): wherein R is methyl or ethyl group have been synthesized. The compounds of formula (I) are potent inhibitors of degranulation of both mast cells and eosinophils. These compounds also suppress cytokines generation by leukocytes. These biological activities are relevant to the prevention and/or treatment of asthma, allergies and inflammatory diseases. It is known to the art that inhibitors of mast cell degranulation such as cromolyn sodium and nedocromil sodium are used in the treatment of asthma and other allergic diseases. Inhibitors of cytokine generation, such as steroids, are also useful in the prevention and treatment of inflammatory diseases as well as asthma and allergies”.
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- Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents
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Several new aryl substituted pyrazol-3-one 3 derivatives were prepared by the reaction of substituted phenyl hydrazine 1 with diethylethoxymethylene malonate (DEEM) 2. The compounds were synthesized by Michael addition reaction, which is a nucleophilic addition of enolate anions to the carbon-carbon double bond of α,β-unsaturated carboxylic acid derivatives. All the compounds were characterized by UV, IR and NMR spectroscopy and tested for hypoglycemic activity on alloxan induced diabetic rats. Among the tested compounds ethyl-2-para nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3c and ethyl-2-meta nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3d are identified as potent hypoglycemic agents and their activities are comparable with the standard drug metformin.
- Das, Nirupam,Verma, Abhilasha,Shrivastava, Prabhat K.,Shrivastava, Sushant K.
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experimental part
p. 1555 - 1558
(2009/04/07)
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- SELECTIVE HYDROGENATION OF NITROGEN CONTAINING AROMATICS
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The present invention describes an improved catalyst and process for the selective hydrogenation of nitro aromatics, nitrosoaromatics and aromatic hydroxyl amines to their corresponding amines using gaseous hydrogen, in the presence of soluble iron compounds as a catalyst and optionally other reducible groups.
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Page/Page column 6-7
(2008/06/13)
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- Scandium(III) catalysis of transimination reactions. Independent and constitutionally coupled reversible processes
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Sc(OTf)3 efficiently catalyzes the self-sufficient transimination reaction between various types of C=N bonds in organic solvents, with turnover frequencies up to 3600 h-1 and rate accelerations up to 6 × 105. The mechanism of the crossover reaction in mixtures of amines and imines is studied, comparing parallel individual reactions with coupled equilibria. The intrinsic kinetic parameters for isolated reactions cannot simply be added up when several components are mixed, and the behavior of the system agrees with the presence of a unique mediator that constitutes the core of a network of competing reactions. In mixed systems, every single amine or imine competes for the same central hub, in accordance with their binding affinity for the catalyst metal ion center. More generally, the study extends the basic principles of constitutional dynamic chemistry to interconnected chemical transformations and provides a step toward dynamic systems of increasing complexity.
- Giuseppone, Nicolas,Schmitt, Jean-Louis,Schwartz, Evan,Lehn, Jean-Marie
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p. 5528 - 5539
(2007/10/03)
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