Iodine-mediated oxidative triple functionalization of indolines with azoles and diazonium salts

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(34), P. 4613 - 4616

Published: Jan. 1, 2024

We report an innovative synthetic strategy for the generation of polysubstituted indoles from indolines, aryldiazonium salts, and azoles. The methodology encompasses electrophilic substitution reaction affording C5-indoline intermediates which undergo iodine-mediated oxidative transformation coupled with C-H functionalization to yield indole derivatives.

Language: Английский

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Recent Progress in Gold‐Catalyzed Reactions of Alkynes for the Construction of Indole Frameworks

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: June 21, 2023

Abstract Indole heterocycles hold an important position in chemical landscape because of their prominence natural products and pharmaceuticals. Consequently, development new efficient strategies to access indole scaffold are continuous interest. For the past few years, gold‐catalyzed activation alkyne has emerged as a powerful strategy for constructing heterocyclic skeleton. The present review highlights recent advances (2018–2023) toward synthesis skeletons via annulations alkynes. A variety alkynes, such as, ynamides, azido ortho ‐alkynyl anilines, propargylic alcohols, phenylimines, miscellaneous alkynes employed affording various architectures under gold catalysis. Moreover, mechanisms included most cases better understanding reaction pathway.

Language: Английский

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Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2607 - 2612

Published: Jan. 1, 2024

A metal-free, scalable, and cascade protocol for assembling diverse polysubstituted pyridines from tertiary enaminones α,β-unsaturated sulfonylketimines by cleaving C–N/N–S bonds is reported.

Language: Английский

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Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10272 - 10282

Published: July 5, 2024

The exploration of remote functionalization indoles is impeded by the inherently dominant reactivity intrinsic to pyrrole moiety. Herein, we delineate a novel strategy facilitated Lewis acid mediation, enabling C-H functionalization, which culminates in synthesis an array selectively functionalized indole derivatives, encompassing 3-trifluoroacetyl and 5-benzoyl motifs, utilizing trifluoroacetic anhydride various acyl chlorides. Notably, protocol exhibits versatility, as epitomized extension C5-acylation alkylation sulfonation reactions. This methodology distinguished its exemplary regio- chemo-selectivity, extensive substrate scope, commendable tolerance diverse functional groups, employment comparatively mild reaction conditions.

Language: Английский

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Chemical discovery of a novel MD2/ADAM17 dual-target inhibitor as a potential therapeutic candidate for saturated fatty acid-induced myocardial inflammatory injury

Metabolism, Journal Year: 2025, Volume and Issue: unknown, P. 156298 - 156298

Published: May 1, 2025

Language: Английский

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Efficient Catalytic Condensation of Methyl Ketones with Indole to Form All‐Carbon Quaternary Center Bisindolylmethanes Mediated by Strong Dual Brønsted Acid

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

Abstract This study develops a protocol for synthesizing bisindolylmethanes (BIMs) with all‐carbon quaternary centers using dual Brønsted acid catalyst ( 1a ) containing two meta‐positioned perfluorobutylsulfonimide groups. The activates aliphatic and aromatic methyl ketones in methanol at 30 °C, yielding 59%–99% BIMs products, acetophenone showing >90% selectivity. Under harsher conditions (e.g., high acetone concentration or loading), formation from drops to <16%, while tetrahydrocyclopenta[b]indole 4 becomes dominant (54%–77% yield), indicating indole substituents’ electronic control over pathway selection. Solvent‐dependent 1 H NMR studies demonstrate hydrogen‐bond‐driven modulation of 's strength, explaining solvent‐dependent These findings highlight substrate‐catalyst complementarity governing product selectivity, providing framework designing strength‐tunable systems synthesis.

Language: Английский

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[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

ACS Omega, Journal Year: 2023, Volume and Issue: 8(31), P. 27894 - 27919

Published: July 25, 2023

Polycyclic fused indoles are ubiquitous in natural products and pharmaceuticals due to their immense structural diversity biological inference, making them suitable for charting broader chemical space. Indole-based polycycles continue be fascinating as well challenging targets synthetic fabrication because of characteristic frameworks possessing biologically intriguing compounds both origin. As a result, an assortment new processes catalytic routes has been established provide unified access these skeletons very efficient selective manner. Transition-metal-catalyzed processes, particular from rhodium(III), widely used endeavors increase molecular complexity efficiently. In recent years, this resulted significant progress reaching scaffolds with enormous activity based on core indole skeletons. Additionally, Rh(III)-catalyzed direct C–H functionalization benzannulation protocols moieties were one the most alluring techniques generate indole-fused polycyclic molecules This review sheds light developments toward synthesizing by cascade annulation methods using Rh(III)-[RhCp*Cl2]2-catalyzed pathways, which align comprehensive sophisticated field functionalization. Here, we looked at few cascade-based designs catalyzed Rh(III) that produced elaborate inspired bioactivity. The also strongly emphasizes mechanistic insights 1–2, 2–3, 3–4-fused systems, focusing routes. With emphasis efficiency product diversity, chosen carbocycles heterocycles least three fused, bridged, or spiro cages reviewed. newly created synthesis concepts toolkits accessing diazepine, indol-ones, carbazoles, benzo-indoles, illustrative privileged techniques, included featured collection.

Language: Английский

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Catalyst-Controlled Diastereoselective Synthesis of Bridged [3.3.1] Bis(Indolyl)-Oxanes and Oxepanes via Desymmetrization of Bis(Indolyl)-Cyclohexadienones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(17), P. 3034 - 3039

Published: April 24, 2023

A catalyst-controlled divergent synthesis of bridged [3.3.1] bis(indolyl)-oxanes and cis-[6.7] fused bis(indolyl) oxepanes via diastereoselective desymmetrization bis(indolyl)-cyclohexadienones is presented for the first time. The reaction highly atom- step-economic, furnishing sp3-rich functionalized derivatives in good to excellent yields with wide substrate scope. proceeds through Friedel-Crafts alkylation followed by selective C-C bond formation/rearrangement. Gram scale synthetic utility generate alkaloid-like molecular diversity were also illustrated.

Language: Английский

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Graphene oxide-catalysed carbene-transfer reaction in water: a highly “green” and selective approach to access 3,3′,3′′-trisindoles

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(4), P. 1990 - 1999

Published: Dec. 21, 2023

A highly “green” and efficient method to furnish biologically important 3,3′,3′′-trisindoles via a graphene oxide-catalysed carbene-transfer reaction of 3-diazo oxindole as carbene precursor with indoles is described.

Language: Английский

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Photocatalytic synthesis of small-molecule drugs by porous framework materials

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(3), P. 109065 - 109065

Published: Sept. 9, 2023

Language: Английский

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