Cargando…

Theoretical Study on the Epimerization of Azlactone Rings: Keto–Enol Tautomerism or Base-Mediated Racemization?

[Image: see text] Azlactones are versatile heterocycles employed in a diversity of transformations; the main drawback of these cycles consists in the epimerization of the α-carbonyl stereocenter during its preparation. We hereby present a theoretical study to explain how the racemization occurs. Two...

Descripción completa

Detalles Bibliográficos
Autores principales:	de Castro, Pedro P., Batista, Gabriel M. F., dos Santos, Hélio F., Amarante, Giovanni W.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2018
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641619/ https://www.ncbi.nlm.nih.gov/pubmed/31458601 http://dx.doi.org/10.1021/acsomega.8b00060

Ejemplares similares

Keto-Enol Tautomerism in Passerini and Ugi Adducts
por: Pertejo, Pablo, et al.
Publicado: (2021)

Lignin Intermediates on Palladium: Insights into Keto‐Enol Tautomerization from Theoretical Modelling
por: de Andrade, Ageo Meier, et al.
Publicado: (2020)

A Brønsted base-promoted diastereoselective dimerization of azlactones
por: Pinheiro, Danielle L J, et al.
Publicado: (2017)

High-yield and sustainable synthesis of quinoidal compounds assisted by keto–enol tautomerism
por: Wang, Cheng, et al.
Publicado: (2021)

First-Principles Study of the Dispersion Effects in the Structures and Keto–Enol Tautomerization of Curcumin
por: Madinah, Roichatul, et al.
Publicado: (2023)

DFT Study To Explore the Importance of Ring Size and Effect of Solvents on the Keto–Enol Tautomerization Process of α- and β-Cyclodiones
por: Jana, Kalyanashis, et al.
Publicado: (2018)

Ultrafast Charge Relocation Dynamics in Enol–Keto Tautomerization Monitored with a Local Soft-X-ray Probe
por: Soley, Micheline B., et al.
Publicado: (2022)

New Precursors to 3-Sulfanylhexan-1-ol? Investigating the Keto–Enol Tautomerism of 3-S-Glutathionylhexanal
por: Muhl, Jennifer R., et al.
Publicado: (2021)

Dual-Mode Multiple Ion Sensing via Analyte-Specific Modulation of Keto–Enol Tautomerization of an ESIPT Active Pyrene Derivative: Experimental Findings and Computational Rationalization
por: Paul, Suvendu, et al.
Publicado: (2023)

Synthesis, Spectroscopic Studies and Keto-Enol Tautomerism of Novel 1,3,4-Thiadiazole Derivative Containing 3-Mercaptobutan-2-one and Quinazolin-4-one Moieties
por: Mohammed, Sewara J., et al.
Publicado: (2020)

Acid epimerization of 20-keto pregnane glycosides is determined by 2D-NMR spectroscopy
por: García, Víctor P.
Publicado: (2011)

Synthesis, Biochemical Characterization, and Theoretical Studies of Novel β-Keto-enol Pyridine and Furan Derivatives as Potent Antifungal Agents
por: Tighadouini, Said, et al.
Publicado: (2020)

Brønsted Acid-Catalyzed Epimerization-Free Preparation of Dual-Protected Amino Acid Derivatives
por: de Castro, Pedro P., et al.
Publicado: (2017)

The enzymatic epimerization of deoxynivalenol by Devosia mutans proceeds through the formation of 3-keto-DON intermediate
por: Hassan, Yousef I., et al.
Publicado: (2017)

Use of activated enol ethers in the synthesis of pyrazoles: reactions with hydrazine and a study of pyrazole tautomerism
por: Tarabová, Denisa, et al.
Publicado: (2014)

Favipiravir tautomerism: a theoretical insight
por: Antonov, Liudmil
Publicado: (2020)

Investigating the Spectroscopy of the Gas Phase Guanine–Cytosine Pair: Keto versus Enol Configurations
por: Botti, Giacomo, et al.
Publicado: (2023)

Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation
por: Manimaran, S., et al.
Publicado: (2018)

Unravelling the Keto–Enol Tautomer Dependent Photochemistry and Degradation Pathways of the Protonated UVA Filter Avobenzone
por: Berenbeim, Jacob A., et al.
Publicado: (2020)

Construction of highly-stable covalent organic framework with combined enol-imine and keto-enamine linkages
por: Jiang, Jian, et al.
Publicado: (2023)

Breslow Intermediates (Amino Enols) and Their Keto Tautomers: First Gas‐Phase Characterization by IR Ion Spectroscopy
por: Paul, Mathias, et al.
Publicado: (2020)

Enol-mediated delivery of H(2)Se from γ-keto selenides: mechanistic insight and evaluation
por: Hankins, Rynne A., et al.
Publicado: (2022)

Voltage-driven control of single-molecule keto-enol equilibrium in a two-terminal junction system
por: Tang, Chun, et al.
Publicado: (2023)

Synthesis of 4-Hydroxycarbazole Derivatives by Benzannulation of 3-Nitroindoles with Alkylidene Azlactones
por: Cao, Dongdong, et al.
Publicado: (2021)

Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization
por: Wang, Xiao-Lin, et al.
Publicado: (2022)

Catalytic asymmetric direct aldol reaction of α-alkyl azlactones and aliphatic aldehydes
por: Zheng, Yang, et al.
Publicado: (2015)

Two RmlC homologs catalyze dTDP-4-keto-6-deoxy-d-glucose epimerization in Pseudomonas putida KT2440
por: Koller, Franziska, et al.
Publicado: (2021)

Epimerization of ergot alkaloids in feed
por: Schummer, Claude, et al.
Publicado: (2020)

Methionine epimerization in cyclic peptides
por: Jadhav, Pramodkumar D., et al.
Publicado: (2021)

Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates
por: Eitzinger, Andreas, et al.
Publicado: (2018)

Enzymatic C4‐Epimerization of UDP‐Glucuronic Acid: Precisely Steered Rotation of a Transient 4‐Keto Intermediate for an Inverted Reaction without Decarboxylation
por: Borg, Annika J. E., et al.
Publicado: (2022)

Peptide Epimerization Machineries Found in Microorganisms
por: Ogasawara, Yasushi, et al.
Publicado: (2018)

Experimental and theoretical study on structure-tautomerism among edaravone, isoxazolone, and their heterocycles derivatives as antioxidants
por: Queiroz, Auriekson N., et al.
Publicado: (2020)

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents
por: Radi, Smaail, et al.
Publicado: (2015)

Gas-Phase Thermal Tautomerization of Imidazole-Acetic Acid: Theoretical and Computational Investigations
por: Aziz, Saadullah G., et al.
Publicado: (2015)

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach
por: Fahmy, Amin F. M., et al.
Publicado: (2016)

NAD(+)‐Dependent Enzymatic Route for the Epimerization of Hydroxysteroids
por: Tonin, Fabio, et al.
Publicado: (2018)

Tautomerism of 4,4(′)-dihydroxy-1,1(′)-naphthaldazine studied by experimental and theoretical methods
por: Ahmedova, Anife, et al.
Publicado: (2013)

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates
por: Chen, Wenyong, et al.
Publicado: (2014)

Tautomeric Forms of Metarhodopsin
por: Matthews, Rowena G., et al.
Publicado: (1963)

Cannot write session to /tmp/vufind_sessions/sess_k2kg283g7r7ve0ve5u7adfksfk