Access to Variously Substituted 5,6,7,8-Tetrahydro-3H-quinazolin-4-ones via Diels–Alder Adducts of Phenyl Vinyl Sulfone to Cyclobutene-Annelated Pyrimidinones

2006 ◽  
Vol 2006 (12) ◽  
pp. 2753-2765 ◽  
Author(s):  
Suryakanta Dalai ◽  
Vladimir N. Belov ◽  
Shamil Nizamov ◽  
Karsten Rauch ◽  
Dirk Finsinger ◽  
...  
Keyword(s):  
Diels Alder ◽  
Vinyl Sulfone ◽  
Phenyl Vinyl

scholarly journals Synthesis, Molecular Docking, Druglikeness Analysis, and ADMET Prediction of the Chlorinated Ethanoanthracene Derivatives as Possible Antidepressant Agents

2020 ◽  
Vol 10 (21) ◽  
pp. 7727
Author(s):  
Mujeeb A. Sultan ◽  
Mansour S. A. Galil ◽  
Mohyeddine Al-Qubati ◽  
Mufeed M. Omar ◽  
Assem Barakat
Keyword(s):  
Molecular Docking ◽  
Steric Effect ◽  
Diels Alder ◽  
Vinyl Sulfone ◽  
Nmr Spectrum ◽  
Antidepressant Agents ◽  
Anti Isomer ◽  
Further Development ◽  
Depressant Drug ◽  
Phenyl Vinyl

Ethanoanthracene cycloadducts (5–7) anti, (5–7) syn, and (5–7) dec have been synthesized from the Diels–Alder (DA) reaction of diene 1,8-dichloroanthracene 2, with the dienophiles; acrylonitrile 3, 1-cynavinyl acetate 4, and phenyl vinyl sulfone 5, individually. The steric effect of dienophile substituents were more favorable toward the anti-isomer formation as deduced from 1H-NMR spectrum. The cheminformatics prediction for (5–7) anti and (5–7) syn was investigated. The in silico anticipated anti-depression activity of the (5–7) anti and (5–7) syn compounds were investigated and compared to maprotiline 9 as reference anti-depressant drug. The study showed that steric interactions play a crucial role in the binding affinity of these compounds to the representative models; 4xnx, 2QJU, and 3GWU. The pharmacokinetic and drug-like properties of (5–7) anti and (5–7) syn exhibited that these compounds could be represented as potential candidates for further development into antidepressant-like agents.

scholarly journals Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone

2016 ◽  
Vol 2016 ◽  
pp. 1-5 ◽  
Author(s):  
Mujeeb A. Sultan ◽  
Usama Karama
Keyword(s):  
Nmr Spectra ◽  
Steric Effect ◽  
Substituent Effects ◽  
Alder Reaction ◽  
Diels Alder ◽  
Vinyl Sulfone ◽  
Diels Alder Reaction ◽  
Phenyl Vinyl

Diels-Alder reaction of 10-allyl-1,8-dichloroanthracene (3) with 2-chloroacrylonitrile (4) and 1-cyanovinyl acetate (5) gives exclusively theorthoisomer while its reaction with phenyl vinyl sulfone (10) yields a mixture of two isomeric adducts with priority toorthoisomer. The reactions proceeded under microwave condition in xylene. Configurations of these isomers have been assigned with the help of NMR spectra. The results indicated that the steric effect is dominating toward the isomer regioselectivity in the Diels-Alder reaction of the present compounds.

scholarly journals A novel LC-MS method development and validation for the determination of phenyl vinyl sulfone in eletriptan hydrobromide

2021 ◽  
Vol 7 (1) ◽  
Author(s):  
Indhu Priya Mabbu ◽  
G. Sumathi ◽  
N. Devanna
Keyword(s):  
Method Development ◽  
Limit Of Detection ◽  
Vinyl Sulfone ◽  
Limit Of Quantification ◽  
Relative Standard ◽  
Pressure Chemical Ionization ◽  
Pressure Chemical ◽  
Development And Validation ◽  
Phenyl Vinyl

Abstract Background The aim of the present method is to develop and validate a specific, sensitive, precise, and accurate liquid chromatography-mass spectrometry (LC-MS) method for the estimation of the phenyl vinyl sulfone in the eletriptan hydrobromide. The effective separation of the phenyl vinyl sulfone was achieved by the Symmetry C18 (50 × 4.6 mm, 3.5 μm) column and a mobile phase composition of 0.1%v/v ammonia buffer to methanol (5:95 v/v), using 0.45 ml/min flow rate and 20 μl of injection volume, with methanol used as diluent. The phenyl vinyl sulfone was monitored on atomic pressure chemical ionization mode mass spectrometer with positive polarity mode. Results The retention time of phenyl vinyl sulfone was found at 2.13 min. The limit of detection (LOD) and limit of quantification (LOQ) were observed at 1.43 ppm and 4.77 ppm concentration respectively; the linear range was found in the concentration ranges from 4.77 to 27.00 ppm with regression coefficient of 0.9990 and accuracy in the range of 97.50–102.10%. The percentage relative standard deviation (% RSD) for six replicates said to be injections were less than 10%. Conclusion The proposed method was validated successfully as per ICH guidelines. Hence, this is employed for the determination of phenyl vinyl sulfone in the eletriptan hydrobromide.

scholarly journals Crystal structure of (2R*,3aR*)-2-phenylsulfonyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole

2017 ◽  
Vol 73 (1) ◽  
pp. 85-87
Author(s):  
Yaiza Hernández ◽  
Isidro Marcos ◽  
Narciso M. Garrido ◽  
Francisca Sanz ◽  
David Diez
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Dipolar Cycloaddition ◽  
Vinyl Sulfone ◽  
Compound C ◽  
Phenyl Vinyl

The title compound, C12H15NO3S, was prepared by 1,3-dipolar cycloaddition of 3,4-dihydro-2H-pyrrole 1-oxide and phenyl vinyl sulfone. In the molecule, both fused five-membered rings display a twisted conformation. In the crystal, C—H...O hydrogen bonds link neighbouring molecules, forming chains running parallel to thebaxis.

scholarly journals Efficiency and Selectivity Aspects in the C–H Functionalization of Aliphatic Oxygen Heterocycles by Photocatalytic Hydrogen Atom Transfer

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 803-808 ◽  
Author(s):  
Carlotta Raviola ◽  
Davide Ravelli
Keyword(s):  
Hydrogen Atom ◽  
Uv Light ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Vinyl Sulfone ◽  
Cyclic Carbonates ◽  
Aromatic Ketones ◽  
Oxygen Heterocycles ◽  
Selectivity Studies ◽  
Phenyl Vinyl

The C–H to C–C conversion in aliphatic oxygen heterocycles (dioxolanes, 1,3-dioxane, or cyclic carbonates) by photocatalytic hydrogen atom transfer and subsequent trapping of the resulting radical with phenyl vinyl sulfone was investigated. The performance of three different photocatalysts, namely tetrabutylammonium decatungstate and the aromatic ketones thioxanthone and 9-fluorenone, was compared. The UV-light-absorbing decatungstate anion is more efficient and permits the use of a smaller excess of hydrogen donor than the aromatic ketones, although the ketones could be excited by visible light. Further intramolecular selectivity studies revealed that aromatic ketones afforded a higher proportion of functionalization at the acetalic versus the ethereal positions than did the decatungstate anion.

ChemInform Abstract: Synthesis of Polyhydroxylated Derivatives of Phenyl Vinyl Sulfone as Structural Analogues of Chalcones.

ChemInform ◽  
2010 ◽  
Vol 32 (43) ◽  
pp. no-no
Author(s):  
Marek T. Konieczny ◽  
Barbara Horowska ◽  
Antoni Kunikowski ◽  
Jerzy Konopa ◽  
Konstanty Wierzba ◽  
...  
Keyword(s):  
Vinyl Sulfone ◽  
Structural Analogues ◽  
Derivatives Of ◽  
Phenyl Vinyl

Reductive Addition of Alkyl Radical to Phenyl Vinyl Sulfone

1992 ◽  
Vol 21 (11) ◽  
pp. 2169-2172 ◽  
Author(s):  
Hideo Togo ◽  
Masahiko Aoki ◽  
Masataka Yokoyama
Keyword(s):  
Alkyl Radical ◽  
Vinyl Sulfone ◽  
Phenyl Vinyl
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