- TEMPO-mediated Aza-diels-alder reaction: Synthesis of tetrahydropyridazines using ketohydrazones and olefins
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A novel, facile, and efficient method for the synthesis of tetrahydropyridazines by a one-pot tandem reaction of easily accessible ketohydrazones and olefins in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) has been successfully developed. The reaction involves the initial generation of azoalkenes from direct oxidative dehydrogenation of ketohydrazones using TEMPO as the commercially available oxidant, followed by a subsequent aza-Diels-Alder reaction with olefins.
- Yang, Xiu-Long,Peng, Xie-Xue,Chen, Fei,Han, Bing
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- Synthesis, crystallographic, computational and molecular docking studies of new acetophenone-benzoylhydrazones
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Three aroylhydrazones, acetophenone-Benzoylhydrazone (I), p-hydroxy-acetophenone-benzoylhydrazone (II) and p-nitro- acetophenone-benzoylhydrazone (III) have been synthesized and further analyzed with the aid of IR, UV-Vis, and NMR spectroscopic and X-ray Crystallographic techniques. The optimized molecular structures were determined by Density Functional Theory (DFT) using the B3LYP function comprising the 6-311++G (2d, 2p) basis set. The calculated and experimental results for the NMR spectroscopic technique were observed to be consistent. The two reported crystals are monoclinic in the same space group of P21/c. Hirshfeld surface analyses revealed H···H as the most important intermolecular interactions in compounds II and III. The molecular docking of the compounds against three enzymes - aldose reductase, aldehyde reductase, and β-glucosidase were also carried out where compound III displayed the best inhibition of the enzymes with a binding energy of -11.30, -9.58 and -11.10 Kcal mol?1 against aldose reductase, aldehyde reductase, and β- glucosidase respectively.
- Ajayeoba, Temitope A.,Woods, Joseph O.,Ayeni, Ayowole O.,Ajayi, Tomilola J.,Akeem, Raji A.,Hosten, Eric C.,Akinyele, Olawale F.
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- Efficient [(NHC)Au(NTf2)]-catalyzed hydrohydrazidation of terminal and internal alkynes
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The efficient hydrohydrazidation of terminal (6a–r, 18 examples, 0.1–0.2 mol % [(NHC)Au(NTf2)], T = 60 °C) and internal alkynes (7a–j, 10 examples, 0.2–0.5 mol % [(NHC)Au(NTf2)], T = 60–80 °C) utilizing a complex with a sterically demanding bispentiptycenyl-substituted NHC ligand and the benign reaction solvent anisole, is reported.
- Heidrich, Maximillian,Plenio, Herbert
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supporting information
p. 2080 - 2086
(2020/09/18)
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- I2-Promoted [4 + 2] cycloaddition of: In situ generated azoalkenes with enaminones: Facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines
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A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judici
- Baell, Jonathan B.,Feng, Jiajun,He, Tiantong,Huang, Fei,Xie, Yuxing,Yu, Yang
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supporting information
p. 9483 - 9493
(2020/12/15)
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- Copper catalyzed cyanomethylation reaction of 4-thiazolidinone
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An effective copper catalyzed Cross Dehydrogenative Coupling (CDC) reaction of 4-thiazolidinones with acetonitrile has been developed. The described strategy undergoes radical pathway by employing copper, oxidant and easily available acetonitrile as a cya
- Chauhan, Prakashsingh M.,Morja, Mayur I.,Asamdi, Manjoorahmed,Chikhalia, Kishor H.
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supporting information
(2020/11/17)
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- Copper catalysed cross-dehydrogenative coupling (CDC) reaction of 4-thiazolidinone with terminal alkyne
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Cross dehydrogenative coupling (CDC) strategy has been employed for C-alkynylation of 4-thiazolidinone with terminal alkyne under copper catalysis. Present reaction involves coupling of C(sp3) adjacent to sulfur of 4-thiazolidinone with C(sp) of terminal alkyne under CDC strategy is unprecedented to the best of our knowledge. Significant functional group tolerance, considerable yield and DFT study for mechanism make this synthetic task more interesting and compatible.
- Shaikh, Mohammedumar M.,Patel, Anuj P.,Chikhalia, Kishor H.
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p. 475 - 485
(2019/01/04)
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- Acetophenone benzoylhydrazones as antioxidant agents: Synthesis, in vitro evaluation and structure-activity relationship studies
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Acetophenone and its analogues are naturally-occurring compounds found in many foods and plants. In this study, a series of acetophenone benzoylhydrazones 5a-o were designed and synthesized as new potential antioxidant agents. Designed molecules contain hydrazone and phenolic hydroxyl moieties which possibly contribute to antioxidant activity. The antioxidant properties of compounds 5a-o in terms of reducing ability and radical-scavenging activity were assessed by using FRAP and DPPH tests, respectively. While the unsubstituted compound 5a had the superior capacity in the FRAP assay, the 2,4-dihydroxyacetophenone analogue 5g was the most potent radical scavenger in the DPPH method. The antioxidant potential of representative compounds 5a and 5g was further confirmed by TEAC and ORAC assays. Cell viability assays revealed that while the promising compounds 5a and 5g had no significant toxicity against HepG2 and NIH3T3 cells, they potently protected HepG2 cells against H2O2-induced oxidative damage at low concentrations. Furthermore, spectroscopic studies with different biometals demonstrated that 5g was able to interact with Cu2+ to form a 1:1 complex.
- Emami, Saeed,Esmaili, Zahra,Dehghan, Gholamreza,Bahmani, Maryam,Hashemi, Seyedeh Mahdieh,Mirzaei, Hassan,Shokrzadeh, Mohammad,Moradi, Seyed Ershad
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p. 292 - 299
(2018/06/29)
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- Palladium-Catalyzed Carbonylative Synthesis of 3-Methyleneisoindolin-1-ones from Ketimines with Hexacarbonylmolybdenum(0) as the Carbon Monoxide Source
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An interesting procedure for the palladium-catalyzed carbonylative synthesis of 3-methyleneisoindolin-1-ones from ketimines was established. By using Mo(CO)6 (0.3 equiv.) as the solid CO source and through C(sp2)?H bond activation, t
- Wang, Zechao,Zhu, Fengxiang,Li, Yahui,Wu, Xiao-Feng
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- Transfer hydrogenation of ketones catalysed by half-sandwich (η6-p-cymene) ruthenium(II) complexes incorporating benzoylhydrazone ligands
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Neutral half-sandwich η6-p-cymene ruthenium(II) complexes of general formula [Ru(η6-p-cymene)Cl(L)] (HL?=?monobasic O, N bidendate benzoylhydrazone ligand) have been synthesized from the reaction of [Ru(η6-p-cymene)(μ-Cl)Cl]2 with acetophenone benzoylhydrazone ligands. All the complexes have been characterized using analytical and spectroscopic (Fourier transform infrared, UV–visible, 1H NMR, 13C NMR) techniques. The molecular structures of three of the complexes have been determined using single-crystal X-ray diffraction, indicating a pseudo-octahedral geometry around the ruthenium(II) ion. All the ruthenium(II) arene complexes were explored as catalysts for transfer hydrogenation of a wide range of aromatic, cyclic and aliphatic ketones with 2-propanol using 0.1?mol% catalyst loading, and conversions of up to 100% were obtained. Further, the influence of other variables on the transfer hydrogenation reaction, such as base, temperature, catalyst loading and substrate scope, was also investigated.
- Mohan, Nanjan,Ramesh, Rengan
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- Synthesis and characterisation of cycloruthenated benzhydrazone complexes: Catalytic application to selective oxidative cleavage of olefins to aldehydes
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A simple and convenient method to synthesise new air-stable cyclometalated ruthenium(ii) complexes from the reaction of p-substituted acetophenone benzhydrazide ligands and [RuHCl(CO)(AsPh3)3] has been described. The complexes have been characterised by various methods, including elemental analysis, FT-IR, NMR (1H and 13C) and UV-vis. The molecular structures of complexes 3 and 4 have been determined by singlecrystal X-ray diffraction analysis which indicates the tridentate coordination mode of the ligand and the presence of a distorted octahedral geometry around the ruthenium ion. The complexes have been found to be a highly active catalytic system in the selective oxidative cleavage of a wide range of alkenes and alkynes in the presence of NaIO4 as an oxidant. Notably, the desired aldehyde products were obtained with high conversions and yields using 0.5 mol% catalyst loading within 30 min at room temperature. Furthermore, the influence of reaction parameters such as solvents, oxidants, temperature and catalyst loading was also investigated.
- Manikandan, Thimma Sambamoorthy,Ramesh, Rengan,Semeril, David
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p. 97107 - 97115
(2016/10/25)
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- Synthesis, structure and anticancer activity of (η6-benzene) ruthenium(II) complexes containing aroylhydrazone ligands
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New benzene ruthenium(II) aroylhydrazone complexes of general molecular formula [Ru(η6-C6H6)Cl(L)] (where L = aroylhydrazone ligand) have been synthesized from the reaction of the precursor [Ru(η6-C6H
- Mohan, Nanjan,Muthumari, Subramanian,Ramesh, Rengan
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- I2-TBHP-catalyzed oxidative cross-coupling of N -sulfonyl hydrazones and isocyanides to 5-aminopyrazoles
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I2-TBHP-catalyzed oxidative cross coupling of N-sulfonyl hydrazones with isocyanides has been realized for the synthesis of 5-aminopyrazoles through formal [4 + 1] annulation via in situ azoalkene formation. Notable features are the metal/alkyn
- Senadi, Gopal Chandru,Hu, Wan-Ping,Lu, Ting-Yi,Garkhedkar, Amol Milind,Vandavasi, Jaya Kishore,Wang, Jeh-Jeng
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supporting information
p. 1521 - 1524
(2015/03/30)
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- Reductive alkylation of hydrazine derivatives with α-picoline-borane and its applications to the syntheses of useful compounds related to active pharmaceutical ingredients
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An efficient method for the direct reductive alkylation of hydrazine derivatives with α-picoline-borane has been developed to synthesize a variety of N-alkylhydrazine derivatives. This method provided N,N-dialkylhydrazine derivatives and N-monoalkylhydrazine derivatives upon fine-tuning of the substrates and the reagent equivalency in a one-pot manner. The method was applied to the synthesis of active pharmaceutical ingredients of therapeutic drugs such as isocarboxazid.
- Kawase, Yasushi,Yamagishi, Takehiro,Kato, Jun-Ya,Kutsuma, Teruo,Kataoka, Tadashi,Iwakuma, Takeo,Yokomatsu, Tsutomu
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p. 455 - 464
(2014/03/21)
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- Direct catalytic asymmetric reductive amination of simple aromatic ketones
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A green method for chiral amine synthesis, the direct catalytic asymmetric reductive amination, was developed. Phenylhydrazide is an ideal nitrogen source for reductive amination. Molecular sieves play dual roles in this reaction. They help to remove Hsu
- Chang, Mingxin,Liu, Shaodong,Huang, Kexuan,Zhang, Xumu
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supporting information
p. 4354 - 4357
(2013/09/24)
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- Benzoylhydrazones in catalytic hydrophosphorylation
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Reactions of benzoylhydrazones derived from heterocyclic and aromatic aldehydes and aliphatic, heterocyclic, and aliphatic-aromatic ketones with diethyl phosphite in the presence of [tetra(tert-butyl)phthalocyanine]aluminum chloride afford α-benzoylhydraz
- Matveeva,Podrugina,Kolesnikova,Zefirov
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experimental part
p. 411 - 417
(2011/02/17)
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- Reactions of β-aminopropionic acid N′-acylhydrazides with carbonyl compounds
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The reactions of β-aminopropionic acid N′-acylhydrazides with aromatic and heterocyclic aldehydes and acetone afford compounds that exist in solutions predominantly as mixtures of 2-substituted 3- acylaminotetrahydropyrimidin-4-ones (ATHP) and tautomeric Schiff's bases. These compounds in the crystalline state probably have structures of ATHP. The ratio of tautomers depends on the type of substituent in the aromatic ring and solvent. The reactions of 2-aryl-3-benzamidotetrahydropyrimidin-4-ones with carboxylic or sulfonic acid chlorides afford derivatives of 1-acyl- and 1-tosyl-3-benzamidotetrahydropyrimidin-4-ones.
- Smirnov,Sizova,Luk'yanov
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p. 635 - 640
(2007/10/03)
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- Efficient solid-state synthesis of aroylhydrazones and ferrocenyl aroylhydrazones
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A novel method for preparing acylhydrazone derivatives by the reaction of aroylhydrazine or heteoaroylhydrazine with corresponding aldehydes, ketones, or 1,1′-diacetylferrocene in the presence of TsOH under solvent-free conditions, is described, The main
- Liu, Wan-Yi,Chen, Bao-Hua,Wu, Xiao-Li,Liang, Yong-Min,Liu, Wei-Min,Ma, Yong-Xiang
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p. 607 - 609
(2007/10/03)
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- Some aryl semicarbazones possessing anticonvulsant activities
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A number of aryl semicarbazones displayed anticonvulsant activity in the maximal electroshock (MES) and subcutaneous pentylenetetrazone (scPTZ) screens when administered intraperitoneally to mice.When given by the oral route to rats, protections was affor
- Dimmock, J. R.,Sidhu, K. K.,Tumber, S. D.,Basran, S. K.,Chen, M.,et al.
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p. 287 - 302
(2007/10/02)
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- Catalytic asymmetric reductive amination of ketones via highly enantioselective hydrogenation of the C=N double bond
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We describe a convenient, chemoselective asymmetric reductive amination procedure for the conversion of ketones to chiral hydrazines and amines. The key step in the three-step process is enantioselective DuPHOS-Rh-catalyzed hydrogenation of the C=N double bond of N-acylhydrazones. Detailed optimization studies revealed the effect of solvent, temperature, and the N- acyl group on the enantioselectivity and catalytic efficiency of the reaction. The reduction products, N-acylhydrazines, were converted to hydrazines or amines through hydrolysis or treatment with samarium(II) iodide, respectively.
- Burk, Mark J.,Martinez, Jose P.,Feaster, John E.,Cosford, Nick
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p. 4399 - 4428
(2007/10/02)
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- Preparation of optically active hydrazines and amines
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A process for the asymmetric hydrogenation of N-acylhydrazones to optically active N-acylhydrazines in the presence of a chiral phospholane catalyst complex, a process for the reductive N--N bond cleavage of N-acylhydrazine to amines with samarium diiodide, and a multistep process for converting keto group-bearing compounds to the corresponding optically active amino group-bearing compounds are disclosed.
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