scholarly journals Highly diastereoselective cascade [5 + 1] double Michael reaction, a route for the synthesis of spiro(thio)oxindoles

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Vahid Saberi ◽  
Ashkan Karimi
Keyword(s):  
Density Functional ◽  
Leishmania Donovani ◽  
Michael Reaction ◽  
Density Functional Theory Calculations ◽  
Docking Studies ◽  
Binding Affinities ◽  
Functional Theory ◽  
Relative Configuration ◽  
Work Up ◽  
Green Conditions

AbstractThe first diastereoselective synthesis of spirothiooxindoles is reported via the Michael reaction between thiooxindoles and dibenzalacetones. The reaction was conducted without any catalyst or additive under green conditions, i.e., ethanol as the solvent and at room temperature. In addition, the described robust method benefits from scalability, simple work-up, and column chromatography-free purification. This work demonstrates the art of governing regio- and stereoselectivity, which has been discussed in the light of Density Functional Theory calculations. Our method represents the first synthesis of spiro[cyclohexanone-thiooxindoles] with the relative configuration of the aryl moieties at the cyclohexanone ring as cis. The obtained cis-spirothiooxindoles, can be used to afford cis-spirooxindoles, which their synthesis had not been explored before. According to our molecular docking studies, cis-spirooxindoles demonstrate higher binding affinities than corresponding trans-spirooxindoles for the OPRT domain of the Leishmania donovani uridine 5′-monophosphate synthase (LdUMPS). Thus, the reported method may eventually be utilized to develop new hit compounds for leishmaniasis treatment.

Synthesis and structure of a coordination polymer based on 6-furylpurine

2016 ◽  
Vol 71 (10) ◽  
pp. 1051-1055
Author(s):  
Indranil Sinha ◽  
Jutta Kösters ◽  
Jens Müller
Keyword(s):  
Coordination Polymer ◽  
Metal Binding ◽  
Density Functional ◽  
Density Functional Theory Calculations ◽  
Binding Affinities ◽  
Purine Derivative ◽  
Functional Theory ◽  
Binding Behavior ◽  
Nitrogen Donor ◽  
Aqueous Conditions

AbstractThe synthesis and structure of [Ag(9-methyl-6-furylpurine)(NO3)]n are reported. The title compound represents a rare example of a purine derivative metalated at all three endocyclic nitrogen atoms. It forms a two-dimensional coordination polymer comprising 14-membered trinuclear metallacycles. Density functional theory calculations helped to understand the metal-binding behavior of the 6-furylpurine moiety by showing the silver(I)-binding affinities of all three nitrogen donor atoms to be essentially identical under aqueous conditions.

scholarly journals Design, synthesis, crystal structure, in vitro cytotoxicity evaluation, density functional theory calculations and docking studies of 2-(benzamido) benzohydrazide derivatives as potent AChE and BChE inhibitors

RSC Advances ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 154-167
Author(s):  
Naghmana Kausar ◽  
Shahzad Murtaza ◽  
Muhammad Nadeem Arshad ◽  
Rahman Shah Zaib Saleem ◽  
Abdullah M. Asiri ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Density Functional Theory ◽  
Density Functional ◽  
Density Functional Theory Calculations ◽  
Docking Studies ◽  
In Vitro Cytotoxicity ◽  
Methyl Anthranilate ◽  
Functional Theory ◽  
Design Synthesis

2-(Benzamido) benzohydrazide derivatives: synthesis from methyl anthranilate and application as potent anti-Alzheimer's agents.

scholarly journals Highly Diastereoselective Cascade [5+1] Double Michael Reaction, a Route for The Synthesis of Spiro Thio-Oxindoles

2021 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Vahid Saberi ◽  
Ashkan Karimi
Keyword(s):  
Room Temperature ◽  
Michael Reaction ◽  
Theoretical Calculations ◽  
Docking Studies ◽  
Binding Affinities ◽  
Diastereoselective Synthesis ◽  
Reaction Products ◽  
High Yields ◽  
Stereo Selectivity ◽  
Green Conditions

Abstract The first diastereoselective synthesis of spiro-thiooxindole is reported via Michael reaction between thiooxindoles and divinyl ketones. The reaction was conducted without any catalyst or additive under green conditions, i.e., ethanol as the solvent and room temperature. This study showed the art of governing regioselectivity in which novel spiro frameworks were generated in high yields. In addition to simple and column chromatography-free purification, the high diastereoselectivity makes this protocol very robust. The regio- and stereo- selectivity of the reaction has been discussed in light of the theoretical calculations, and molecular docking has been performed on the reaction products. Our method presents the first synthesis of cis-spiro thiooxindoles, which can be used to generate cis-spiro oxindoles. According to our docking studies, the latter demonstrates higher binding affinities towards the LdUMPS than corresponding trans-spiro oxindoles and may be utilized to develop new hit compounds for leishmaniasis treatment.

THE REACTION MECHANISMS OF ALDEHYDES AND NITROSTYRENE CATALYZED BY A CHIRAL SILYLATED PYRROLIDINE CATALYST

2013 ◽  
Vol 12 (03) ◽  
pp. 1350004
Author(s):  
LI-HUA GAN ◽  
JIN ZHOU ◽  
XIAO GUO
Keyword(s):  
Density Functional ◽  
Michael Reaction ◽  
Enantiomeric Excess ◽  
Density Functional Theory Calculations ◽  
Reaction Pathways ◽  
Functional Theory ◽  
Substituent Group ◽  
Excess Value ◽  
Asymmetric Michael Reaction ◽  
Good Agreement

The asymmetric Michael reaction of aldehydes and nitrostyrene catalyzed by a new (S)-tertbutyl-diphenyl-silyl-pyrrolidine catalyst has been investigated by using density functional theory calculations. The Re face of the enamine is effectively shielded, because of the bulky 2-substituent group on the pyrrolidine ring. For acetaldehyde, there are two different conformers of enamines. Based on the two conformers of enamines, four different reaction pathways have been considered. The calculated enantiomeric excess value is 80.27% in favor of the (R)-configuration product. For propanal, eight different reaction pathways have been considered and the eight corresponding transition states have been located. The calculated enantiomeric excess value is 98.96% in favor of the (2S, 3R)-configuration product. These calculated results are in good agreement with the experimental observations. In addition, the calculations also show that both the used solvent and the enamines play important roles in determining the stereochemical outcome of the product.

On the Linear Geometry of Lanthanide Hydroxide (Ln—OH, Ln=La-Lu)

2019 ◽  
Author(s):  
Hassan Harb ◽  
Lee Thompson ◽  
Hrant Hratchian
Keyword(s):  
Triple Bond ◽  
Density Functional ◽  
Valence Electron ◽  
Density Functional Theory Calculations ◽  
Electron Configuration ◽  
Functional Theory ◽  
Key Species ◽  
Pi Orbitals ◽  
Lanthanide Hydroxide ◽  
Linear Geometry

Lanthanide hydroxides are key species in a variety of catalytic processes and in the preparation of corresponding oxides. This work explores the fundamental structure and bonding of the simplest lanthanide hydroxide, LnOH (Ln=La-Lu), using density functional theory calculations. Interestingly, the calculations predict that all structures of this series will be linear. Furthermore, these results indicate a valence electron configuration featuring an occupied sigma orbital and two occupied pi orbitals for all LnOH compounds, suggesting that the lanthanide-hydroxide bond is best characterized as a covalent triple bond.

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