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A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water Heteroat. Chem. (IF 0.862) Pub Date : 2021-01-04 Alemayehu Mekonnen; Alemu Tesfaye
Tandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The
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Understanding the Mechanism and Selectivities of the Reaction of Meta-Chloroperbenzoic Acid and Dibromocarbene with β-Himachalene: A DFT Study Heteroat. Chem. (IF 0.862) Pub Date : 2020-09-18 Sana El Hamidi; Malika Khnifira; El Mokhtar Lemdek; Redouan Hammal; Noureddine Barka; M’hamed Sadiq; Ahmed Benharref; Ahmed Chekroun; Hssaine Zgou; Mohamed Abdennouri
This study was performed to understand the site selectivity in the reaction between β-himachalene and meta-chloroperbenzoic acid (m-CPBA) in the first step followed by the addition of dibromocarbene (CBr2) to the main monoepoxidation product Pα formed in the first reaction. Calculations were performed using the Becke three-parameter hybrid exchange functional and the Lee–Yang–Parr correlation functional
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Synthesis of Some Novel Fluorinated/Nonfluorinated α-Amino Acids, Bearing 3-Thioxo-5-oxo-1,2,4-triazin-6-yl and Steroidal Moieties, and Evaluation of Their Amylolytic Effects against Some Fungi, Part-II Heteroat. Chem. (IF 0.862) Pub Date : 2020-07-23 Reda M. Abdel-Rahman; Wafa A. Bawazir
Some new fluorinated/nonfluorinated α-amino acids bearing 3-thioxo-5-oxo-1,2,4-triazin-6-yl and steroidal moieties have been obtained from condensation of the corresponding amino-triazinones with the steroid (Epiandrosterone). This was followed by the addition of HCN and, finally, acidic hydrolysis. The structure of the targets was established from their elemental analysis and spectral data. The amylolytic
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Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles Heteroat. Chem. (IF 0.862) Pub Date : 2020-07-08 Hassan Kabirifard; Pardis Hafez Taghva; Hossein Teimouri; Niloofar Koosheshi; Parastoo Javadpour; Hanieh Bagherinejad; Soheila Seyfi; Maryam Hossein Roodbari; Elaheh Golabian
The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led
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Efficient ZrO(NO3)2.2H2O Catalyzed Synthesis of 1H-Indazolo[1,2-b] phthalazine-1,6,11(13H)-triones and Electronic Properties Analyses, Vibrational Frequencies, NMR Chemical Shift Analysis, MEP: A DFT Study Heteroat. Chem. (IF 0.862) Pub Date : 2020-03-01 Forozan Piryaei; Nahid Shajari; Hooriye Yahyaei
The synthesis of 1H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione derivatives, using one-pot three-component condensation reaction of 3-nitrophthalic anhydride, hydrazine monohydrate, dimedone, and aromatic aldehydes in the presence of ZrO(NO3)2.2H2O as the novel catalyst and in reflux conditions in EtOH was reported. Quantum theoretical calculations for three structures of compounds (5a, 5b, and 5c)
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Dichlorophosphoranides Stabilized by Formamidinium Substituents Heteroat. Chem. (IF 0.862) Pub Date : 2020-02-13 Anatoliy Marchenko; Georgyi Koidan; Anastasiya Hurieva; Eduard Rusanov; Alexander B. Rozhenko; Aleksandr Kostyuk
Dichlorophosphoranides featuring N,N-dimethyl-N′-arylformamidine substituents were isolated as individual compounds. Dichlorophosphoranide 9 was prepared by the multicomponent reaction of C-trimethylsilyl-N,N-dimethyl-N′-phenylformamidine and N,N-dimethyl-N′-phenylformamidine with phosphorus trichloride. Its molecular structure derived from a single-crystal X-ray diffraction was compared to the analogous
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Synthesis of New Oxindoles and Determination of Their Antibacterial Properties Heteroat. Chem. (IF 0.862) Pub Date : 2020-02-08 Pablo E. Romo; Braulio Insuasty; Rodrigo Abonia; María del Pilar Crespo; Jairo Quiroga
A versatile method for the synthesis of new oxindoles was developed by the reaction between substituted isatins and 5-aminopyrazoles. The reaction was carried out at room temperature in ethanol using p-toluenesulfonic acid as the catalyst. The products were obtained with acceptable to excellent yields (44–96%). Structures of the new compounds were unambiguously established by spectroscopic and analytical
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10H-Pyrazino[2,3-b][1,4]benzotellurazine, a Novel Tellurium-Containing Heterocyclic System Heteroat. Chem. (IF 0.862) Pub Date : 2020-01-11 Diamond S. Smith; Dallas N. Alexis; Frank R. Fronczek; Thomas Junk
Condensation of 2,3-dichloropyrazine with 2-aminobenzenetellurole and 2-amino-5-methylbenzenetellurole, generated in situ by reduction of the corresponding ditellurides, resulted in the formation of novel 10H-pyrazino[2,3-b][1,4]benzotellurazine and its 7-methyl derivative. The products were purified via their well-crystallized 5,5-dibromo derivatives. X-ray crystallographic analysis of the title compound
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2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands Heteroat. Chem. (IF 0.862) Pub Date : 2019-10-09 Marzena Wosińska-Hrydczuk; Jacek Skarżewski
New epoxides, derivatives of pyridine, 2,2′-bipyridine, and 1,10-phenanthroline, were synthesized from the respective α-methylazaarenes. The obtained racemic 2-oxiranyl-azaarenes along with styrene oxide and trans-stilbene oxide were submitted to the ring opening with chiral primary amines as a chiral auxiliary. The most effective reaction was run in the presence of Sc(OTf)3/diisopropylethylamine for
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Synthesis of Some New 1,2,4-Triazine and 1,2,5-Oxadiazine Derivatives with Antimicrobial Activity Heteroat. Chem. (IF 0.862) Pub Date : 2019-09-25 Heba E. Hashem; Ahmed M. Abo-Bakr
1,2,4-Triazine and 1,2,5-oxadiazine derivatives 2–12 were obtained from treated 1,3-oxazolone (1) with phenyl hydrazine or hydroxylamine hydrochloride. Chlorotriazine derivative 3 undergoing condensation reactions with different reagents produced new fused tetrazolo-triazine and triazino-quinazolinone derivatives. 1,2,5-Oxadiazine has been used as a synthon for the fused pyrazolo-oxadiazine derivative
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Cyclopentadienyl Ruthenium(II) Complex-Mediated Oxidation of Benzylic and Allylic Alcohols to Corresponding Aldehydes Heteroat. Chem. (IF 0.862) Pub Date : 2019-08-18 Ching-Yuh Chern; Ching-Chun Tseng; Rong-Hong Hsiao; Fung Fuh Wong; Yueh-Hsiung Kuo
This work reports an efficient method for the oxidation reaction of aliphatic, aromatic allylic, and benzylic alcohols into aldehydes catalyzed by the cyclopentadienyl ruthenium(II) complex (RuCpCl(PPh3)2) with bubbled O2. Through further optimizing controlled studies, the tendency order of oxidation reactivity was determined as follows: benzylic alcohols > aromatic allylic alcohols >> aliphatic alcohols
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Theoretical Prediction for Synthetic Realization: Pyramidal Systems ClE[E′4R4] (E = B–Ga, E′ = C–Ge, R = SiMe3, SiMetBu2): A DFT Study Heteroat. Chem. (IF 0.862) Pub Date : 2019-07-22 Olga A. Gapurenko; Vladimir Ya. Lee; Ruslan M. Minyaev; Vladimir I. Minkin
Structure and bonding of hybrid group 13/14 pyramidal molecules ClE[R4] (E = B–Ga, E′ = C–Ge, R = SiMe3, SiMetBu2) were studied by DFT calculations. Six pyramidal structures are suggested for their potential synthetic realization.
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Synthesis of Benzothiophene-Fused Pyran Derivatives via Piperidine Promoted Domino Reaction Heteroat. Chem. (IF 0.862) Pub Date : 2019-05-02 Shihang Li; Aimin Yu; Jianfa Li; Xiangtai Meng
A new domino reaction between thioaurones and malononitrile has been reported. This reaction allows efficient access to benzothiophene-fused pyran derivatives in good yields under mild reaction conditions. The substrate scope is broad; a series of benzothiophene-fused pyran derivatives have been synthesized.
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Host-Guest Complexations of Amine Boranes and Isoelectronic/Isostructural Quaternary Alkylammonium Cations by Cucurbit[7]uril in Aqueous Solution Heteroat. Chem. (IF 0.862) Pub Date : 2019-04-14 Mona A. Gamal-Eldin; Donal H. Macartney
The host-guest complexation of six amine boranes (R3NBH3) by the macrocyclic host molecule cucurbituril (CB) in aqueous solution has been investigated using 1H and 11B NMR spectroscopy. The limiting complexation-induced 1H and 11B chemical shift changes indicate that the amine boranes are included in the hydrophobic cavity of the host molecule. The host-guest stability constants for neutral R3NBH3∙CB
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[4+2] versus [2+2] Homodimerization in P(V) Derivatives of 2,4-Disubstituted Phospholes Heteroat. Chem. (IF 0.862) Pub Date : 2019-04-01 Guillaume Bousrez; Emmanuel Nicolas; Agathe Martinez; Sylviane Chevreux; Florian Jaroschik
Phosphole P(V) derivatives are interesting building blocks for various applications from ligand synthesis to material sciences. We herein describe the preparation and characterisation of new 2,4-disubstituted oxo-, thiooxo-, and selenooxophospholes. The nature of the substituents on the phosphole ring determines the reactivity of these compounds towards homodimerization reactions. Aryl and trimethylsilyl
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Computational Studies of 4-Formylpyridinethiosemicarbazone and Structural and Biological Studies of Its Ni(II) and Cu(II) Complexes Heteroat. Chem. (IF 0.862) Pub Date : 2019-03-03 Mydhili P. Sripathi; Sireesha Berely; Chittireddy Venkata Ramana Reddy
To understand the stability, chelation behaviour, and biological activity of 4-Formylpyridinethiosemicarbazone (H4FPT), it is important to recognize its interactive geometry. Hence, computational studies on geometrically optimized structures of thione and thiol forms of H4FPT were performed. Binary metal complexes of the ligand, H4FPT (L) with the Ni(II) and Cu(II) metal ions (M), were synthesized
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SN-Donor Methylthioanilines and Copper(II) Complexes: Synthesis, Spectral Properties, and In Vitro Antimicrobial Activity Heteroat. Chem. (IF 0.862) Pub Date : 2019-03-03 Temitope E. Olalekan; Adeniyi S. Ogunlaja; Gareth M. Watkins
Methylthioanilines, a series of sulfur-nitrogen donor ligands substituted with OCH3, CH3, Cl, and Br, and their copper(II) complexes have been synthesized and characterized by 1H and 13C NMR, elemental analysis, FTIR, UV-Vis and EPR spectra, molar conductance, and magnetic susceptibility measurements. The NMR spectra of the ligands revealed that the para/ortho protons and para carbon were sensitive
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One-Pot Synthesis of Hypervalent Diaryl(iodo)bismuthanes from o-Carbonyl Iodoarenes by Zincation Heteroat. Chem. (IF 0.862) Pub Date : 2019-02-27 Toshihiro Murafuji; A. F. M. Hafizur Rahman; Daiki Magarifuchi; Masahiro Narita; Isamu Miyakawa; Katsuya Ishiguro; Shin Kamijo
Diaryl(iodo)bismuthanes possessing a hypervalent C=O•••Bi–I bond were conveniently synthesized in a one-pot reaction by using arylzinc reagents generated from o-carbonyl iodobenzenes and zinc powder under ultrasonication. This method is superior to the conventional organolithium and Grignard methods because it has a wide functional group tolerance, requires no protecting group manipulations, and proceeds
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On the Reactivity of N-tert-Butyl-1,2-Diaminoethane: Synthesis of 1-tert-Butyl-2-Imidazoline, Formation of an Intramolecular Carbamate Salt from the Reaction with , and Generation of a Hydroxyalkyl-Substituted Imidazolinium Salt Heteroat. Chem. (IF 0.862) Pub Date : 2019-02-05 Kieren J. Evans; Ben Potrykus; Stephen M. Mansell
N-tert-Butyl-1,2-diaminoethane was shown to react rapidly with atmospheric carbon dioxide to generate the zwitterionic ammonium carbamate salt CO2N(H)C2H4NBu (1). Reaction of N-tert-butyl-1,2-diaminoethane with triethylorthoformate gave 1-tert-butyl-2-imidazoline (2) in 24% yield after fractional distillation, and the hydroxyalkyl-tethered imidazolinium salt [HOC(Me)2CH2NC2H4N(CH)tBu][Cl] (3) was synthesised
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Thiazole Based Carbohydrazide Derivatives as α-Amylase Inhibitor and Their Molecular Docking Study Heteroat. Chem. (IF 0.862) Pub Date : 2019-02-04 Muhammad Taha; Maryam Irshad; Syahrul Imran; Fazal Rahim; Manikandan Selvaraj; Noor Barak Almandil; Ashik Mosaddik; Sridevi Chigurupati; Faisal Nawaz; Nor Hadiani Ismail; Mohamed Ibrahim
In this study we are going to present thiazole based carbohydrazide in search of potent antidiabetic agent as α-amylase inhibitors. Thiazole based carbohydrazide derivatives 1-25 have been synthesized, characterized by 1HNMR, 13CNMR, and EI-MS, and evaluated for α-amylase inhibition. Except compound 11 all analogs showed α-amylase inhibitory activity with IC50 values from 1.709 ± 0.12 to 3.049 ± 0
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Tautomeric Equilibria in Solutions of 2-Phenacylbenzimidazoles Heteroat. Chem. (IF 0.862) Pub Date : 2019-02-03 Agnieszka Skotnicka; Przemysław Czeleń; Ryszard Gawinecki
Detailed NMR spectral analysis of DMSO-d6 solutions of the series of substituted 2-phenacylbenzimidazoles (ketimine form, K) reveals two from three tautomeric forms. Integrals of the 1H NMR signals are used in establishing the molar ratio of tautomers. The experimental analyses are supported by quantum-chemical calculations, which satisfactorily reproduced the experimental trends. Although the reported
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N-Heterocyclic Germylenes: Structural Characterisation of Some Heavy Analogues of the Ubiquitous N-Heterocyclic Carbenes Heteroat. Chem. (IF 0.862) Pub Date : 2019-01-23 Christopher A. Dodds; Alan R. Kennedy; Mark D. Spicer
The X-ray crystal structures of three N-heterocyclic germylenes (NHGes) have been elucidated including the previously unknown 1,3-bis(2,6-dimethylphenyl)diazagermol-2-ylidene (1). In addition, the X-ray crystal structures of the previously synthesised 1,3-bis(2,4,6-trimethylphenyl)diazagermol-2-ylidene (2) and 1,3-bis(2,6-diisopropylphenyl)diazagermol-2-ylidene (3) are also reported. The discrete molecular
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A Thermochemical Parameters and Theoretical Study of the Chlorinated Compounds of Thiophene Heteroat. Chem. (IF 0.862) Pub Date : 2019-01-09 Ibrahim A. M. Saraireh; Mohammednoor Altarawneh; Jibril Alhawarin; Mansour H. Almatarneh
This contribution sets out to compute thermochemical and geometrical parameters of the complete series of chlorinated isomers of thiophene based on the accurate chemistry model of CBS-QB3. Herein, we compute standard entropies, standard enthalpies of formation, standard Gibbs free energies of formation, and heat capacities. Our calculated enthalpy values agree with available limited experimental values
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Imidazole and Azo-Based Schiff Bases Ligands as Highly Active Antifungal and Antioxidant Components Heteroat. Chem. (IF 0.862) Pub Date : 2019-01-03 Siham Slassi; Adeline Fix-Tailler; Gérald Larcher; Amina Amine; Abdelkrim El-Ghayoury
We describe, herein, the synthesis, full characterization, and optical properties of four different ligands L1-L4 which associate an azo group, an imidazole unit, and a Schiff base fragment. The UV-visible absorption bands are characteristic of and transitions with an additional charge transfer between the azobenzene moiety and the imino group. Finally the determination of MIC80 values against pathogenic
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Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted Heteroat. Chem. (IF 0.862) Pub Date : 2019-01-02 Semih Kurban; Nahide Gulsah Deniz; Cigdem Sayil; Mustafa Ozyurek; Kubilay Guclu; Maryna Stasevych; Viktor Zvarych; Olena Komarovska-Porokhnyavet; Volodymyr Novikov
A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus
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An Efficient Selectfluor-Mediated Oxidative Thio- and Selenocyanation of Diversely Substituted Indoles and Carbazoles Heteroat. Chem. (IF 0.862) Pub Date : 2019-01-02 Rodrigo Abonia; Luisa F. Gutierrez; Angela T. Zwarycz; Sebastián Correa Smits; Kenneth K. Laali
A facile Selectfluor-mediated oxidative method for direct introduction of SCN and SeCN groups into diversely substituted indoles and carbazoles is described, by employing readily available thiocyanate and selenocyanate salts, and the scope of the method is underscored by providing 24 examples. The feasibility to sequentially introduce SCN followed by SeCN on a carbazole framework and to synthesize