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Journal articles on the topic 'Stereochemistry of Hydrazones'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Vojinovic-Jesic, Ljiljana, Sladjana Novakovic, Vukadin Leovac, and Valerija Cesljevic. "Transition metal complexes with Girard reagents and their hydrazones." Journal of the Serbian Chemical Society 77, no. 9 (2012): 1129–55. http://dx.doi.org/10.2298/jsc120704083v.

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This is the first review dealing with the coordination chemistry of metal complexes with Girard's reagents and their hydrazones. The short introduction points out to chemical properties and significance of these organic compounds. The next section briefly describes synthetic methods for preparing complexes with Girard's reagents, as well as modes of coordination of these ligands. The last two extensive sections review the preparation, stereochemistry and structural characteristics of metal complexes with Girard's hydrazones, including some newer non-hydrazonic derivatives of Girard's reagents,

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2

MRIDULA, VERMA, and M. VERMA SHIVA. "Hydrogen Bonding and the Stereochemistry of Hydrazones and Hydrazides derived from 1,3-Dicarbonyl Compounds involving Imino Nitrogen." Journal of Indian Chemical Society Vol. 69, Sep 1992 (1992): 561–62. https://doi.org/10.5281/zenodo.6006453.

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Department of Chemistry, Banaras Hindu University, Varanasi-221 005 <em>Manuscript received 5 August 1991, revised 8 June 1992, accepted 3 July 1992</em> <em>β</em>-Diketones form hydrazones with <em>N' ,N'</em> -diacylhydrazines and exhibit a six-membered hydrogen bonded cyclic ketiminyl system involving the imino nitrogen. <sup>1</sup>H nmr spectra of the hydrazones obtained from <em>N</em>-amino -α, β- (9,10-dihydroanthracene-9,10-endo-diyl)succinimide and acetylacetone demonstrated restricted rotation about <em>N-N</em> bond and a planer hydrogen bonded cyclic syste

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3

Sivý, Július, Dušan Bortňák, Daniel Végh, and Erik Rakovský. "Two novel potent perfluorophenylhydrazone derivatives, 1-((4-bromothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, and 1-((4-bromo-5-methylthiophen-2-yl)methylene)-2-(perfluorophenyl)hydrazine as multi-target compounds to combat Alzheimer disease and their crystal, molecular, and electronic properties." Acta Chimica Slovaca 16, no. 1 (2023): 81–91. http://dx.doi.org/10.2478/acs-2023-0008.

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Abstract Two potent novel perfluorophenylhydrazone derivatives are presented as multi-target compounds to combat Alzheimer disease C11H4BrF5N2S, 1-((4-bromothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, (I) and C12H6BrF5N2S, 1-((4-bromo-5-methylthiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, (II), which can potentially be improved by further design. Their multi-target structures and features have been combined as potential AD therapeutics. Crystals (I), and (II), are molecules with two rings and a hydrazone part as a centre of the molecule. The compounds have been synthesised

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4

VERMA, M., and S. M. VERMA. "ChemInform Abstract: Hydrogen Bonding and the Stereochemistry of Hydrazones and Hydrazides Derived from 1,3-Dicarbonyl Compounds Involving Imino Nitrogen." ChemInform 24, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.199351130.

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5

Hiroi, Kunio, Nagahisa Yamaoka, Fumiko Kato, and Koki Oishi. "Stereochemistry of asymmetric cyclizations by palladium-catalyzed intramolecular asymmetric allylations of chiral enamines, imines, and hydrazones bearing phosphine groups." Tetrahedron Letters 36, no. 40 (1995): 7251–54. http://dx.doi.org/10.1016/0040-4039(95)01502-9.

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6

HIROI, K., N. YAMAOKA, F. KATO, and K. OISHI. "ChemInform Abstract: Stereochemistry of Asymmetric Cyclizations by Palladium-Catalyzed Intramolecular Asymmetric Allylations of Chiral Enamines, Imines, and Hydrazones Bearing Phosphine Groups." ChemInform 27, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199603083.

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7

YOGENDRA, KUMAR, D. SETHI P., and L. JAIN C. "Spectral, Magnetic, Mossbauer and Chemotherapeutical Studies of lron(III) Complexes with various New Derivatives of lsonicotinic Acid Hydrazide." Journal of Indian Chemical Society Vol. 67, Oct. 1990 (1990): 796–99. https://doi.org/10.5281/zenodo.6243383.

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Central Indian Pharmacopoeia Laboratory, Raj Nagar, Ghaziabad-201 002 Department of Chemistry, M. M. H. College, Ghaziabad-201 001 <em>Manuscript received </em><em>9 </em><em>June </em><em>1989, </em><em>revised </em><em>19 </em><em>June </em><em>1990, </em><em>accepted </em><em>9 </em><em>July </em><em>1990</em>   A number of iron(III) complexes with new hydrazones of  isonicotinic acid hydrazide (INH) have been synthesised having general formula [FeL<sub>2</sub>Cl<sub>2</sub>]Cl, [FeL'<sub>2</sub>]Cl and [FeL"<sub>2</sub>]Cl<sub>3</sub>, where L=bidentate ligands <em>N</em

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8

Kong, Yao, Yuanning Liu, Kaibiao Wang, et al. "Confirmation of the stereochemistry of spiroviolene." Beilstein Journal of Organic Chemistry 20 (April 18, 2024): 852–58. http://dx.doi.org/10.3762/bjoc.20.77.

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We confirm the previously revised stereochemistry of spiroviolene by X-ray crystallographically characterizing a hydrazone derivative of 9-oxospiroviolane, which is synthesized by hydroboration/oxidation of spiroviolene followed by oxidation of the resultant hydroxy group. An unexpected thermal boron migration occurred during the hydroboration process of spiroviolene that resulted in the production of a mixture of 1α-hydroxyspiroviolane, 9α- and 9β-hydroxyspiroviolane after oxidation. The assertion of the cis-orientation of the 19- and 20-methyl groups provided further support for the revised

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9

Amanzhan, A., P. Zh Zhanymkhanova, I. Yu Bagryanskaya, E. E. Shults, A. Zh Turmukhambetov, and S. M. Adekenov. "STRUCTURE AND STEREOCHEMISTRY OF A HYDRAZONE DERIVATIVE OF HARMINE." Journal of Structural Chemistry 62, no. 3 (2021): 491–95. http://dx.doi.org/10.1134/s0022476621030161.

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10

Mabied, Ahmed F., Elsayed M. Shalaby, Hamdia A. Zayed, Esmat El-Kholy, Ibrahim S. A. Farag, and Naima A. Ahmed. "Crystal Structure and Stereochemistry Study of 2-Substituted Benzoxazole Derivatives." ISRN Organic Chemistry 2014 (May 13, 2014): 1–7. http://dx.doi.org/10.1155/2014/728343.

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The structure of 2-[(4-chlorophenylazo) cyanomethyl] benzoxazole, C15H9ClN4O (I), has triclinic (P1̅) symmetry. The structure displays N–H⋯N hydrogen bonding. The structure of 2-[(arylidene) cyanomethyl] benzoxazoles, C17H10N2O3 (II), has triclinic (P1̅) symmetry. The structure displays C–H⋯N, C–H⋯C hydrogen bonding. In (I), the chlorophenyl and benzoxazole groups adopt a trans configuration with respect to the central cyanomethyle hydrazone moiety. Compound (II) crystallized with two molecules in the asymmetric unit shows cisoid conformation between cyano group and benzoxazole nitrogen, contr

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11

Andersen, Denise L., and Thomas G. Back. "Stereochemistry of Cuprate-Mediated Conjugate Additions of a 17-Iodoandrost-16-ene to E- and Z-6-Methylhept-2-en-4-one." Collection of Czechoslovak Chemical Communications 66, no. 12 (2001): 1797–808. http://dx.doi.org/10.1135/cccc20011797.

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(3S,15R)-15-(Benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene (3) was prepared from the corresponding 17-hydrazone 9 with iodine in the presence of tetramethylguanidine. The vinyl iodide 3 was converted into the corresponding organocuprate and conjugate additions of the latter were performed with both (E)- and (Z)-6-methylhept-2-en-4-one (4a and 4b, respectively). In each case, the resulting adduct 5a was obtained exclusively with the unnatural 20S configuration. (3S,15R)-15-(Benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]androsta-5,16-diene (13) and the corresponding 17,17'

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12

Mitu, Liviu, Natarajan Raman, Angela Kriza, Nicolae Stănică, and Mariana Dianu. "Template synthesis, characterization and antimicrobial activity of some new complexes with isonicotinoyl hydrazone ligands." Journal of the Serbian Chemical Society 74, no. 10 (2009): 1075–84. http://dx.doi.org/10.2298/jsc0910075m.

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Complexes of Cu(II), Ni(II), Co(II) with the 9-anthraldehyde isonicotinoyl hydrazone ligand (HL1) and the 3,5-di-tert-butyl-4-hydroxybenzaldehyde isonicotinoyl hydrazone ligand (H2L2) were synthesized by the template method. The complexes were characterized by analytical analysis, IR, UV-Vis and ESR spectroscopy, magnetic measurements, conductometry and thermal analysis and the two ligands by 1H-NMR spectroscopy. From the elemental analysis, 1:2 (metal:ligand) stoichiometry for the complexes of Cu(II), Ni(II) with the ligands HL1 and H2L2 and 1:1 (metal:ligand) stoichiometry for the complex of

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13

Ahmed, Ayman H. "N,N′-Bis[2-hydroxynaphthylidene]/[2-methoxybenzylidene]amino]oxamides and their divalent manganese complexes: Isolation, spectral characterization, morphology, antibacterial and cytotoxicity against leukemia cells." Open Chemistry 18, no. 1 (2020): 426–37. http://dx.doi.org/10.1515/chem-2020-0044.

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AbstractManganese(ii) complexes of oxalic dihydrazones {N,N′-bis[2-hydroxynaphthylidene]amino]oxamide (BHO) and N,N′-bis[2-methoxybenzylidene]amino]oxamide (BMO)} have been synthesized by a general methodology. Hydrazone ligands (BHO and BMO) were obtained by the condensation of oxalic dihydrazide with 2-hydroxynaphthalene-1-carbaldehyde and 2-methoxybenzaldehyde. From the data obtained from the spectral (mass, IR, 1H-NMR, UV-Vis, ESR), magnetic and thermal measurements in addition to the elemental analyses (CHNM), the structures of ligands and their complexes have been determined. The scannin

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14

da Silva, Fernando de C., Vitor F. Ferreira, Patrícia de O. Lopes, James L. Wardell та Solange M. S. V. Wardell. "Stereochemistry of Products of Reactions between 3-diazo-naphthalene-1,2,4-trione and β-dicarbonyl Compounds. Structure of ethyl 2-[(3-hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-hydrazono]-3-phenyl-3-oxo-propionate". Journal of Chemical Research 2009, № 5 (2009): 308–11. http://dx.doi.org/10.3184/030823409x440850.

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3-Hydroxy-2-[(R1CO)(R2CO)]C=NNH-1,4-naphthoquinones, obtained from reactions of 3-diazonaphthalene-1,2,4-trione with β-diketones, R1C(O)CH2COR2, have been previously found to have high antibacterial activity. However, confirmation of the stereochemistry about the C=N bond could not be achieved by spectroscopic means for products having different R1 and R2 groups, thereby limiting the utility of the reaction. Full characterisation of the product isolated from reaction of 3-diazonaphthalene-1,2,4-trione with PhC(O)CH2CO2Et is now reported, from a single crystal X-ray structure determination: the

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15

Mukhtar, Sayeed, Mohammed Issa Al-Ahmdi, and Humaira Parveen. "Synthesis, Stereochemistry and Antimicrobial Activity of Some Novel Flavanone-hydrazono-thiazolidin-4-ones from Flavanones." Asian Journal of Chemistry 28, no. 12 (2016): 2589–95. http://dx.doi.org/10.14233/ajchem.2016.19908.

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16

Zivkovic, Marijana B., Ivana Z. Matic, Marko V. Rodic, et al. "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro." J Steroid Biochem Mol Biol Nov 174 (July 19, 2017): 72–85. https://doi.org/10.1016/j.jsbmb.2017.07.031.

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The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) <strong>4a</strong>–<strong>f</strong> and <strong>5a</strong>–<strong>f</strong> have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (<em>E</em> or <em>Z</em>) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (<em>E</em>)

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17

Galiano-Roth, Angela S., and David B. Collum. "Lithium-6 and sodium-23 NMR spectroscopic studies of metalated hydrazone cryptates. Effects of ion triplet formation on the stereochemistry of alkylation." Journal of the American Chemical Society 110, no. 11 (1988): 3546–53. http://dx.doi.org/10.1021/ja00219a033.

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18

Ramachandran, Rajamanickam, Paramasivam Parthiban, Mannangatty Rani, Sampathkumar Jayanthi, Senthamaraikannan Kabilan, and Yeon Tae Jeong. "Synthesis, stereochemistry and in vitro antimicrobial evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2,3-dihydrothiazoles." Bioorganic & Medicinal Chemistry Letters 21, no. 21 (2011): 6301–4. http://dx.doi.org/10.1016/j.bmcl.2011.08.115.

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19

Galeta, Juraj, Stanislav Man, and Milan Potáček. "Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones." Chemical Papers 67, no. 1 (2013). http://dx.doi.org/10.2478/s11696-012-0215-6.

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AbstractThe paper presents a simple synthesis of substituted propargyl vinyl ethers and their subsequent thermally-initiated Claisen rearrangement leading to various 3-substituted homoallenyl aldehydes. Several methods, including Sonogashira coupling, base-promoted substitution on the triple bond by sodium amide or butyllithium, and the preparation of substituted propargyl alcohols, were used in the initial step. Phosphate-protected homoallenyl aldehyde hydrazone derivatives were synthesised and fully characterised. The stereochemistry of 9-anthracene carbaldehyde hydrazone, which, surprisingl

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20

Calinescu, Mirela, Emilia Ion, Ana Emandi, Rodica Georgescu, and Ticuta Negreanu-Pirjol. "Magnetic, Optical and Biological Studies on Copper(II) Complexes with 2-benzothiazolyl Hydrazones. II." Revista de Chimie 59, no. 12 (2009). http://dx.doi.org/10.37358/rc.08.12.2053.

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Three Cu(II) complex compounds with 4-methoxybenzaldehyde-2-benzothiazolyl hydrazone(HL) have been prepared and characterized by elemental and thermogravimetrical analysis, infrared, electronic and EPR spectra. The complex compounds have various composition and stereochemistry, depending on the reaction conditions and the metal salt used. The ligand acts as neutral bidentate NN donor in the complexes [Cu(HL)2(H2O)2] . Cl2 and [Cu(HL)2(H2O)Br] . Br and monobasic bidentate donor in the complex [Cu2L4]. EPR studies of the complexes gave axial symmetry, with dx2-y2 the ground state. The bonding pa

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21

Аманжан, А., П. Ж. Жанымханова, И. Ю. Багрянская, Э. Э. Шульц, А. Ж. Турмухамбетов, and С. М. Адекенов. "STRUCTURE AND STEREOCHEMISTRY OF A HYDRAZONE DERIVATIVE OF HARMINE." Журнал структурной химии, 2021. http://dx.doi.org/10.26902/jsc_id69943.

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22

Taxak, Bharti, Jai Devi, Amit Dubey, et al. "Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies." Applied Organometallic Chemistry, December 6, 2023. http://dx.doi.org/10.1002/aoc.7323.

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In the search of novel and effective anti‐infectious agents, new hydrazone ligands (1–4) and their diorganotin (IV) complexes (5–20) were synthesized by condensing piperonylic hydrazide with salicylaldehyde derivatives, which have been further characterized by numerous physical and spectral techniques [1H, 13C, 119Sn] NMR, mass spectroscopy, UV–Vis, IR). These techniques ascertained dibasic tridentate coupling of hydrazone ligands with diorganotin (IV) through phenolic, enolic oxygens, and imine nitrogen, demonstrating pentacoordinated stereochemistry of the complexes. The thermal stability of

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23

Kumar, Binesh, Jai Devi, Amit Dubey, and Manish Kumar. "Biological and Computational Studies of Hydrazone based Transition Metal(II) Complexes." Chemistry & Biodiversity, July 22, 2024. http://dx.doi.org/10.1002/cbdv.202401116.

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In the chronicles of human history, infectious diseases played a pivotal role, influencing societies, steering advancements in medicine, and significantly impacting the well‐being of people worldwide. Consequently, in the pursuit of identifying effective combating agents for infectious ailments, the Co(II), Ni(II), Cu(II), Zn(II) complexes of N'‐(4‐nitrobenzylidene)benzohydrazide were synthesized in the current investigation. Numerous spectral and physical analysis were conducted to characterize the compounds which revealed octahedral stereochemistry of complexes. The anti‐tuberculosis, anti‐i

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24

GALIANO-ROTH, A. S., and D. B. COLLUM. "ChemInform Abstract: 6Li and 23Na NMR Spectroscopic Studies of Metalated Hydrazone Cryptates. Effects of Ion Triplet Formation on the Stereochemistry of Alkylation." ChemInform 19, no. 38 (1988). http://dx.doi.org/10.1002/chin.198838076.

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25

da Silva, Fernando de C., Vitor F. Ferreira, Patricia de O. Lopes, James L. Wardell та Solange M. S. V. Wardell. "ChemInform Abstract: Stereochemistry of Products of Reactions Between 3-Diazo-naphthalene-1,2,4-trione and β-Dicarbonyl Compounds. Structure of Ethyl 2-[(3-Hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-hydrazono] -3-phenyl-3-oxo-propionate (III)." ChemInform 40, № 44 (2009). http://dx.doi.org/10.1002/chin.200944102.

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