On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

Beilstein Journal of Organic Chemistry, Год журнала: 2021, Номер 17, С. 1849 - 1938

Опубликована: Июль 30, 2021

Several valuable biologically active molecules can be obtained through C–H activation processes. However, the use of expensive and not readily accessible catalysts complicates process pharmacological application these compounds. A plausible way to overcome this issue is developing using cheaper, more accessible, equally effective catalysts. First-row transition (3d) metals have shown important in matter. This review summarizes 3d metal processes obtain potentially (or proved)

Язык: Английский

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Ruthenium(II)-Catalyzed Sequential C–H/N–H Alkene Annulation Cascade of Phenanthroimidazoles: Synthesis and Photophysical Studies

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6016 - 6026

Опубликована: Апрель 16, 2024

We report ruthenium(II)-catalyzed sequential C–H/N–H alkenylation cascade of phenanthroimidazole and alkenes to form novel phenanthroimidazoisoindol acrylates via dual C–H activation aza-Michael reaction. The two nitrogen atoms the imidazole ring act as directing groups for regioselective ortho activation. These polycyclic N-heterocycles were evaluated their photophysical properties.

Язык: Английский

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Regioselective intramolecular cyclization of o-alkynyl arylamines with the in situ formation of ArXCl to construct poly-functionalized 3-selenylindoles

RSC Advances, Год журнала: 2023, Номер 13(9), С. 6210 - 6216

Опубликована: Янв. 1, 2023

In this article, a practical and metal-free method for the synthesis of poly-functionalized 3-selenyl/sulfenyl/telluriumindoles from

Язык: Английский

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Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4458 - 4494

Опубликована: Ноя. 24, 2023

Abstract The preservation of scarce rare earth metals, such as palladium, rhodium, iridium, and others, poses a significant challenge for humanity due to their limited availability. These metals might be replaced by earth‐abundant 3d‐transition cobalt, manganese, iron, nickel, copper, etc . Isoquinolines have acquired an important position in synthetic organic chemistry well medicinal chemistry. They manifest diverse range natural molecules, serving pivotal synthons the synthesis numerous bioactive compounds with notable significance. Numerous reports on isoquinoline derivatives via transition metal catalysis been published worldwide. In this review, we summarize recent approaches synthesizing various using 3d‐transition‐metal catalysts since 2020. review has divided into different 3d‐transition‐metal‐based catalysis. We expect that will bring better overview present status progress made isoquinolines persuade more advancements research area near future.

Язык: Английский

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Copper-Catalyzed Tandem Radical Cyclization of 8-Ethynyl-1-naphthyl-amines for the Synthesis of 2H-Benzo[e][1,2]thiazine 1,1-Dioxides and its Fluorescence Properties

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(19), С. 12526 - 12534

Опубликована: Сен. 8, 2020

A copper-catalyzed radical cascade dehydrogenative cyclization of N-tosyl-8-ethynyl-1-naphthylamines under air is described herein for the synthesis thioazafluoranthenes. The reaction proceeds smoothly with high efficiency and a broad scope. product indeed new fluorophore its photophysical properties are also investigated. Based on results, we pleased to find that Stokes shift amino-linked thioazafluoranthenes in dilute tetrahydrofuran determined be 143 nm (4830 cm–1).

Язык: Английский

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Construction of Tricyclic Nitrogen Heterocycles by a Gold(I)‐Catalyzed Cascade Cyclization of Allenynes and Application to Polycyclic π‐Electron Systems

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(52), С. 27019 - 27025

Опубликована: Сен. 30, 2021

A novel approach to the direct construction of tricyclic nitrogen heterocycles based on gold-catalyzed cascade cyclization aminoallenynes is described. The expected biscyclization reaction hydroxyisobutyryl-protected was efficiently promoted by a catalytic amount BrettPhosAuNTf2 in presence iPrOH produce 1,2-dihydrobenzo[cd]indole derivatives good yields. When combined with Friedel-Crafts acylation or palladium-catalyzed N-arylation, resulting products were converted into nitrogen-containing polycyclic aromatic compounds (N-PACs) highly conjugated π-electron systems. newly obtained hexacyclic indolium salt showed characteristic concentration-dependent absorption and emission properties.

Язык: Английский

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Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(13), С. 8515 - 8524

Опубликована: Июнь 22, 2022

Here, we report a novel and facile protocol for the synthesis of benz[c,d]indol-2-imines via palladium-catalyzed C–C C–N coupling 8-halo-1-naphthylamines with isocyanides in single step. The reaction features broad substrate scopes mild conditions, providing an efficient alternative construction antiproliferative agents BET bromodomain inhibitors. If 0.1 mL H2O was added to this reaction, N-substituted amino-1-naphthylamides could be obtained easily.

Язык: Английский

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Twofold C−H Activation Enables Synthesis of a Diazacoronene‐Type Fluorophore with Near Infrared Emission Through Isosteric Replacement

Chemistry - A European Journal, Год журнала: 2020, Номер 27(8), С. 2753 - 2759

Опубликована: Окт. 21, 2020

Abstract The synthesis and photophysical properties of a soluble amide‐embedded coronene is reported. key step in this the twofold C−H activation diazaperylene by rhodium(III)Cp* catalyst. This unprecedented structural motif shows intense fluorescence near infrared region with small Stokes shift distinct vibronic structure, which exhibits slight extent negative solvatochromism. Comparison compound some relevant compounds revealed importance amide incorporation peripheral concave including an angular position to retain high aromaticity reflecting that parent coronene. Treatment Lewis acid B(C 6 F 5 ) 3 formed bis‐adduct, exhibited enhanced as consequence increased double bond character C−N bonds.

Язык: Английский

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Synthesis of Fused Tetracyclic Compounds via Oxidative Annulation: Access to Copper-Catalyzed Indolo[1,2-a]quinolines and to Ruthenium-Catalyzed Isoquinolin-1[2H]-ones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5772 - 5779

Опубликована: Апрель 14, 2023

A facile double oxidative annulation of (en-3-yn-1-yl)phenylbenzamides was developed allowing us to synthetize fused tetracyclic compounds. Under copper catalysis, the reaction proceeds with high efficiency and leads new indolo[1,2-a]quinolines via a decarbonylative annulation. On other hand, under ruthenium isoquinolin-1[2H]-ones were obtained

Язык: Английский

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Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(9), С. 6336 - 6346

Опубликована: Апрель 7, 2022

In this work, we developed an efficient method for the rapid construction of fluoranthene skeleton to access a variety substituted hydroxyfluoranthenes. The 1-iodo-8-alkynylnaphthalene derivatives, which serve as substrates key fluoranthene-forming step, were prepared via selective monoalkynylative Sonogashira reactions 1,8-diiodonaphthalene. domino reaction sequence involves sequential Suzuki–Miyaura coupling, intramolecular Diels–Alder reaction, and aromatization-driven ring-opening isomerization has been shown give hydroxyfluoranthenes in up 92% yield. This work demonstrates utility designing new polycyclic aromatic hydrocarbons (PAHs).

Язык: Английский

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