Synthesis of Biologically Active Molecules through Multicomponent Reactions

Molecules, Год журнала: 2020, Номер 25(3), С. 505 - 505

Опубликована: Янв. 24, 2020

Focusing on the literature progress since 2002, present review explores highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of vast number organic molecules, but also, highlights fact many such molecules are biologically active or at least been submitted to any biological screen. The selected papers covered in this must meet two mandatory requirements: (1) reported products should be obtained via reaction; (2) actives tested property. Given diversity synthetic approaches utilized MCRs, diverse nature activities evaluated synthesized compounds, and considering their huge structural variability, much data organized into concise schemes tables facilitate comparison, underscore key points review.

Язык: Английский

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Transition metal-catalyzed coupling of heterocyclic alkenesviaC–H functionalization: recent trends and applications

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(12), С. 1527 - 1569

Опубликована: Янв. 1, 2020

Heterocyclic alkenes and their derivatives are an important class of reactive feedstock valuable synthons. This review highlights the transition-metal-catalyzed coupling heterocyclic alkenesviaa C–H functionalization strategy.

Язык: Английский

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Transition Metal‐Catalysed Direct C−H Bond Functionalizations of 2‐Pyridone Beyond C3‐Selectivity

Chemistry - An Asian Journal, Год журнала: 2020, Номер 15(14), С. 2092 - 2109

Опубликована: Июнь 5, 2020

2-Pyridone is a ubiquitous motif in natural products, drug molecules, ligands catalysis and organic materials. There necessity of direct step-economic methods for the construction 2-pyridone based molecules. Strategically, primary developments have led to C3-functionalizations due inherent reactivity this center. Despite this, many elegant transition metal-catalysed been established introduce versatile functional groups at C4, C5 C6-position via C-H bond functionalizations. This minireview focuses on categorized introduction different scaffolds beyond C3-selectivity discusses substrate scope, limitations plausible mechanistic details.

Язык: Английский

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Ligand-Controlled Ni(0)–Al(III) Bimetal-Catalyzed C3–H Alkenylation of 2-Pyridones by Reversing Conventional Selectivity

ACS Catalysis, Год журнала: 2021, Номер 11(8), С. 4606 - 4612

Опубликована: Апрель 1, 2021

Conventional C–H alkenylation with alkynes via low-valent transition-metal catalysis occurs at the C6 or C4 position of 2-pyridone electron-deficient bonds. A bifunctional ligand-bonded Ni–Al bimetallic catalyst resulted in a reversed selectivity, providing series C3-alkenylated 2-pyridones up to 99% yields.

Язык: Английский

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Site-Selective C–H Arylation of 2-Pyridones via Pd/NBE Cooperative Catalysis

ACS Catalysis, Год журнала: 2024, Номер 14(10), С. 7762 - 7770

Опубликована: Май 3, 2024

The 4-aryl-2-pyridone scaffold is considered to be a privileged pharmacophore. Diversity-oriented synthesis of its derivatives pressing demand within the field medicinal chemistry. Herein, we report site-selective C–H arylation 2-pyridones via palladium/norbornene cooperative catalysis. success this research based on nucleophilicity and metalation properties exhibited by C5 position in 2-pyridones, an activated norbornene that was employed capture C5-palladation intermediate transfer it C4 position, resulting highly specific at position. This methodology showcases remarkable compatibility with readily available aryl bromides, enabling efficient diverse range functional scaffolds (46 examples) notable site selectivity, which will very useful drug discovery. Furthermore, approach successfully utilized for economically viable perlolidine analogues. Density theory calculations revealed preference bond activation 2-pyridones. In addition, insights into mechanism suggest oxidative addition reductive elimination bromides are crucial steps conversion.

Язык: Английский

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Rhodium(i)-catalyzed C6-selective C–H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids

Chemical Science, Год журнала: 2019, Номер 10(43), С. 10089 - 10096

Опубликована: Янв. 1, 2019

A versatile Rh(i)-catalyzed C6-selective decarbonylative C–H alkenylation of 2-pyridones with readily available alkenyl carboxylic acids has been developed.

Язык: Английский

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Rh(I)-Catalyzed C6-Selective Decarbonylative Alkylation of 2-Pyridones with Alkyl Carboxylic Acids and Anhydrides

Organic Letters, Год журнала: 2020, Номер 22(11), С. 4228 - 4234

Опубликована: Май 8, 2020

A Rh-catalyzed chelation-assisted C6-selective C-H activation/alkylation of 2-pyridones with readily available alkyl carboxylic acids or anhydrides is introduced. The reaction proceeds via substrate decarbonylation. This approach merges functionalization anhydrides, allowing for the efficient synthesis various C6-alkylated good functional group tolerance.

Язык: Английский

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Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides

Organic Letters, Год журнала: 2018, Номер 20(17), С. 5167 - 5171

Опубликована: Авг. 24, 2018

A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of 2-pyridone core with easily available aryl iodides. The transformation highly regioselective and accomplished a wide scope functional group tolerance. Silver nitrate played crucial role in this direct site-selective arylation. method extended to synthesize biologically active molecules.

Язык: Английский

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Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step

Chemical Science, Год журнала: 2020, Номер 11(40), С. 11042 - 11054

Опубликована: Янв. 1, 2020

Ligand-enabled switch of the regioselectivity-determining step allowed for efficient regiocontrol in aerobic oxidative Heck reaction indole.

Язык: Английский

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Traceless Directing Groups in Sustainable Metal-Catalyzed C–H Activation

Catalysts, Год журнала: 2021, Номер 11(5), С. 554 - 554

Опубликована: Апрель 27, 2021

Sustainable transformations towards the production of valuable chemicals constantly attract interest, both in terms academic and applied research. C–H activation has long been scrutinized this regard, given that it offers a straightforward pathway to prepare compounds great significance. In context, directing groups (DG) have paved way for chemical had not achievable using traditional reactions. Few steps, high yields, selectivity inert substrates are some invaluable assets directed catalysis. Additionally, employment traceless (TDG) greatly improves simplifies strategy, enabling realization multi-step reactions one-pot, cascade procedures. Cheap, abundant, readily available transition metal salts complexes can catalyze plethora employing TDGs, usually under low catalyst loadings—rarely stoichiometric amounts, leading greater atom economy milder conditions with increased yields step-economy. This review article summarizes all work done on TDG-assisted catalysis manganese, iron, cobalt, nickel, or copper catalysts, discusses structure-activity relationships observed, by presenting catalytic pathways range reported thus far.

Язык: Английский

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