Synthetic enzyme-catalyzed multicomponent reaction for Isoxazol-5(4<i>H</i>)-one Syntheses, their properties and biological application; why should one study mechanisms?

Oliveira, Gabriela H. C.; Ramos, Luciana M.; Paiva, Raíssa Kelly Corrêa de; Passos, Saulo T. A.; Simões, Marina M.; Machado, Fabricio; Corrêa, José R.; Neto, Brenno A. D.

doi:10.1039/d0ob02114h

Cited by 18 publications

(7 citation statements)

References 107 publications

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“…The synthetic enzyme also functioned as a phase‐transfer agent, facilitating the gathering of the reagents in the nanocatalytic system structure, and overcoming the low solubility of the 1,3‐dicarbonyl reagent. Although there are three possible mechanisms to explain this MCR, an ESI‐MS(/MS) investigation characterized the intermediates to reveal that only one was operating under catalyzed conditions with an appropriate solvent [79] . The noncovalent interactions provided by catalyst's imidazolium rings were observed to stabilize the keto tautomer of ethyl acetoacetate (Scheme 6, as supported by NMR spectroscopy).…”

Section: Discussionmentioning

confidence: 98%

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Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

2022

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In the current Perspective article, we critically review and discuss the importance of solvent effects on multicomponent reactions, likely the most neglected aspect in this research field. Although solvent-free reactions may be desirable sometimes, most multicomponent reactions still require a solvent to properly promote them. This requirement makes the knowledge of all drawbacks and advantages of each solvent a central issue when trying to optimize multicomponent reactions. Yet, only a few studies with actual evidence of solvent effects on these key reactions have been published. For the quantitative effects of solvents, studies are even scarcer. In this Perspective, we argue that greater efforts should be directed to such fundamental studies.

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Section: Discussionmentioning

confidence: 98%

“…The MCR synthesis of isoxazol‐5(4H)‐one derivatives was achieved in water using a synthetic enzyme applied as the catalytic system [79] . The solvent effect investigation led to in‐depth comprehension of the transformation and helped to understand the preferred reaction mechanism pathways (Scheme 6).…”

Section: Discussionmentioning

confidence: 99%

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

2022

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“…Mechanistically, the condensation reaction of hydroxylamine and ethyl acetoacetate is followed by cyclization. The resulting isoxazolones undergo a Knoevenagel-type condensation with aromatic aldehydes to form isoxazol-5(4H)-ones 28 in good to excellent yields (Scheme 6B) (Oliveira et al, 2021).…”

Section: Nitrogen Heterocyclesmentioning

confidence: 99%

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

Brandner

Müller²

2023

Front. Chem.

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Multicomponent reactions, conducted in a domino, sequential or consecutive fashion, have not only considerably enhanced synthetic efficiency as one-pot methodology, but they have also become an enabling tool for interdisciplinary research. The highly diversity-oriented nature of the synthetic concept allows accessing huge structural and functional space. Already some decades ago this has been recognized for life sciences, in particular, lead finding and exploration in pharma and agricultural chemistry. The quest for novel functional materials has also opened the field for diversity-oriented syntheses of functional π-systems, i.e. dyes for photonic and electronic applications based on their electronic properties. This review summarizes recent developments in MCR syntheses of functional chromophores highlighting syntheses following either the framework forming scaffold approach by establishing connectivity between chromophores or the chromogenic chromophore approach by de novo formation of chromophore of interest. Both approaches warrant rapid access to molecular functional π-systems, i.e. chromophores, fluorophores, and electrophores for various applications.

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“…We recently applied an MCR to the synthesis of isoxazol-5(4 H )-one (ISX) derivatives, an important class of heterocyclics with potential and diverse biological activities [ 161 , 162 , 163 , 164 , 165 , 166 ], by using a synthetic enzyme (synzyme) that we had previously reported [ 167 ] as an efficient catalyst to perform ISX syntheses ( Scheme 11 ) [ 168 ]. Some of these MCR adducts had fluorescent properties and could be applied in cell-imaging experiments as selective bioprobes.…”

Section: The Combined Role Of Catalysis and Solvent Effects In Mcrsmentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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Synthetic enzyme-catalyzed multicomponent reaction for Isoxazol-5(4H)-one Syntheses, their properties and biological application; why should one study mechanisms?

Abstract: In this work, we describe the application of a synthetic enzyme (synzyme) as the catalyst to promote the multicomponent synthesis of isoxazol-5(4H)-one derivatives. The catalytic system could be used up...

Cited by 18 publications

References 107 publications

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

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