Synthesis of 2-(2-Aminophenyl)-4-arylquinazoline Derivatives by Reaction of 2-Aminoarylbenzimidamides with Isatoic Anhydride

2009 ◽  
Vol 64 (8) ◽  
pp. 945-951 ◽  
Author(s):  
Kamal M. El-Shaieb ◽  
Peter G. Jones
Keyword(s):  
Single Crystal ◽  
Structure Analysis ◽  
High Yield ◽  
Isatoic Anhydride ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Neutral Reaction

A series of 2-(2-aminophenyl)-4-arylquinazoline derivatives (5a - j), with various 4-substituents, have been synthesized by one-pot cyclization in 66 - 79% yield by heating 2-aminoarylbenzimidamides 3a - j with isatoic anhydride (4). The high yield and simplified workup procedure, in addition to the neutral reaction conditions, are the main advantages of our approach. The structure of the product 5e was further confirmed by single-crystal X-ray structure analysis

1,3-Dipolar [3+3] Cycloaddition of 1,4-Benzodiazepinone-Based Nitrones with α-Halohydroxamates for Diastereoselective Synthesis of Novel d-Edge Heterocycle-Fused 1,4-Benzodiazepinones

Synlett ◽  
2021 ◽  
Author(s):  
Hong-Wu Zhao ◽  
Heng Zhang ◽  
Lu-Yu Cai ◽  
Zhe Tang ◽  
Xiao-Zu Fan ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Reaction Mechanism ◽  
Single Crystal ◽  
Structure Analysis ◽  
Crystal Structure Analysis ◽  
Diastereoselective Synthesis ◽  
Reaction Conditions ◽  
Relative Configuration ◽  
X Ray ◽  
Single Crystal Structure Analysis

Promoted by K2CO3 (2.0 equiv), the 1,3-dipolar [3+3] cycloaddition between 1, 4-benzodiazepinone-based nitrones and α-halohydroxamates processed smoothly under the mild reaction conditions and delivered structurally novel and complex cis or trans-configured d-edge-heterocycle-fused 1,4-benzodiazepinones in up to >99% isolated yield with >20:1 dr. The relative configuration of the title chemical entities was clearly identified with the use of X-ray single crystal structure analysis. The reaction mechanism was assumed to interpret the diastereoselective production of the obtained cis or trans-configured d-edge-heterocycle-fused 1, 4-benzodiazepinones.

A Vanadyl(V) Complex with a Pincer-type Thiobis(phenolate) and an Acetylacetonate Co-ligand, VO(tbp)(acac)

2010 ◽  
Vol 65 (12) ◽  
pp. 1457-1461 ◽  
Author(s):  
Rahman Bikas ◽  
Hassan Hosseini Monfared ◽  
Somayeh Alami ◽  
Ingo Pantenburg ◽  
Gerd Meyer
Keyword(s):  
Single Crystal ◽  
Dimethyl Sulfoxide ◽  
Structure Analysis ◽  
Reduction Process ◽  
Vanadium Atom ◽  
High Yield ◽  
X Ray Diffraction ◽  
Cyclic Voltammetric ◽  
X Ray ◽  
Diffraction Structure

A new vanadyl(V) complex with the tridentate, pincer-type O,S,O-ligand thiobis(phenolate), tbp, was synthesized from the reaction of vanadium(IV) oxide bis(acetylacetonate), VO(acac)2, and 2,2’- thio-bis(4-methylphenol), H2tbp, in refluxing methanol in high yield. Single-crystal X-ray diffraction structure analysis revealed for VO(tbp)(acac) that the vanadium atom is octahedrally coordinated with an O5,S-donor environment where the thiobis(phenolate) ligand is O,S,O-bonded to the vanadyl(V) center facially in a tridentate dinegative fashion. Cyclic voltammetric experiments carried out with its solution in dimethyl sulfoxide revealed an irreversible peak at −0.768 V (vs. Ag/AgCl) relating to the V5+/V4+ reduction process.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

2018 ◽  
Vol 15 (3) ◽  
pp. 380-387
Author(s):  
Xia Zhao ◽  
Xiaoyu Lu ◽  
Lipeng Zhang ◽  
Tianjiao Li ◽  
Kui Lu
Keyword(s):  
Double Bond ◽  
Efficient Method ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Antibacterial Activities ◽  
Oxidation Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.

How the Magnetic Field Impacts the Chiroptical Activities of Helical Copper Enantiomers

2021 ◽  
Author(s):  
jialu wu ◽  
Bo Li ◽  
Hong Wang ◽  
Ying Zhen Lai ◽  
Yue Ye ◽  
...  
Keyword(s):  
Magnetic Field ◽  
Solid State ◽  
Thermogravimetric Analysis ◽  
Single Crystal ◽  
Structure Analysis ◽  
Chiral Ligands ◽  
X Ray ◽  
The Magnetic Field

A pair of enantiomers {[Cu(L-pro)(L-tyr)]·2H2O}n (L-1) and {[Cu(D-pro)(D-tyr)]·2H2O}n (D-1) based on the chiral ligands L/D-proline and L/D-tyrosine were synthesized and investigated by single-crystal X-ray structure analysis, IR, thermogravimetric analysis, solid-state...

Replacing sulfonate by carboxylate: application of pyridyliminocarboxylato copper(II) complexes in rac-lactide polymerization and Chan–Evans–Lam coupling

2019 ◽  
Vol 97 (3) ◽  
pp. 178-190 ◽  
Author(s):  
Valérie Hardouin Duparc ◽  
Clémentine Dimeck ◽  
Frank Schaper
Keyword(s):  
Molecular Sieves ◽  
Weight Control ◽  
Phenylboronic Acid ◽  
Side Reactions ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Induction Periods ◽  
Lactide Polymerization

Copper(II) complexes carrying pyridylmethyleneaminobenzoate or –propanoate ligands, LCuX, were prepared in one-pot reactions from pyridinecarboxaldehyde, aminobenzoic acid or β-alanine, and CuX2 (X = Cl, NO3, OAc, or OTf). All complexes were characterized by single-crystal X-ray diffraction studies and formed either dimers, tetramers, or coordination polymers. Attempted preparation of the respective alkoxide complexes, LCu(OR), was unsuccessful, but use of LCuX/NaOMe mixtures in rac-lactide polymerization indicated under some conditions coordination–insertion polymerization via a copper alkoxide as the mechanism. The complexes performed poorly in rac-lactide polymerization, showing low activities (12 h to completion at 140 °C), low to moderate heterotacticity (Pr = 0.6–0.8), and poor polymer molecular weight control (intramolecular transesterification). They were competent catalysts for Chan–Evans–Lam couplings with phenylboronic acid, without any indication of side reactions such as deboration or aryl homocoupling. The complexes were active in undried methanol, without addition of base, ligand, or molecular sieves. Aniline, n-octylamine, and cyclohexylamine were coupled quantitatively under identical reaction conditions. There is only little influence of the anion on activities (less than a factor of 2) but a strong influence on induction periods. The complexes were not active in CEL coupling with alcohols, phenols, or alkylboronic acids.

scholarly journals Arene Ruthenium Metalla-Assemblies with Anthracene Moieties for PDT Applications

Inorganics ◽  
2018 ◽  
Vol 6 (3) ◽  
pp. 97 ◽  
Author(s):  
Marie Gaschard ◽  
Farzaneh Nehzat ◽  
Thomas Cheminel ◽  
Bruno Therrien
Keyword(s):  
Molecular Structure ◽  
Single Crystal ◽  
General Formula ◽  
Structure Analysis ◽  
White Light ◽  
Light Irradiation ◽  
Synthesis And Characterization ◽  
X Ray

The synthesis and characterization of three metalla-rectangles of the general formula [Ru4(η6-p-cymene)4(μ4-clip)2(μ2-Lanthr)2][CF3SO3]4 (Lanthr: 9,10-bis(3,3’-ethynylpyridyl) anthracene; clip = oxa: oxalato; dobq: 2,5-dioxido-1,4-benzoquinonato; donq: 5,8-dioxido-1,4-naphthoquinonato) are presented. The molecular structure of the metalla-rectangle [Ru4(η6-p-cymene)4(μ4-oxa)2(μ2-Lanthr)2]4+ has been confirmed by the single-crystal X-ray structure analysis of [Ru4(η6-p-cymene)4(μ4-oxa)2(μ2-Lanthr)2][CF3SO3]4 · 4 acetone (A2 · 4 acetone), thus showing the anthracene moieties to be available for reaction with oxygen. While the formation of the endoperoxide form of Lanthr was observed in solution upon white light irradiation, the same reaction does not occur when Lanthr is part of the metalla-assemblies.

scholarly journals One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes

2013 ◽  
Vol 9 ◽  
pp. 265-269 ◽  
Author(s):  
Ping-An Wang ◽  
Sheng-Yong Zhang ◽  
Henri B Kagan
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
Single Crystal Diffraction ◽  
One Pot ◽  
X Ray ◽  
Tandem Cyclization

A series of chiral 10-heteroazatriquinanes were synthesized from enantiopure asymmetric cis-2,5-disubstituted pyrrolidines through a one-pot tandem cyclization procedure. The structures and configurations of these new chiral 10-heteroazatriquinanes are confirmed by X-ray single-crystal diffraction analysis.

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