Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4298 - 4302

Published: June 7, 2023

The synthesis of functionalized carbazoles as privileged nitrogen heterocycles has emerged a central topic in drug discovery and material science. We herein disclose the rhodium(III)-catalyzed cross-coupling reaction between indolyl nitrones 2-methylidene cyclic carbonate an allylating surrogate, resulting formation C2-formylated via tandem C–H allylation, [3 + 2] cycloaddition, aromatization, benzylic oxidation. synthetic utility this protocol is highlighted by variety post-transformations carbazoles.

Language: Английский

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Brønsted Acid-Catalyzed Reaction of N-arylnaphthalen-2-amines with Quinone Esters for the Construction of Carbazole and C–N Axially Chiral Carbazole Derivatives

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 2841 - 2850

Published: Feb. 22, 2023

We demonstrated here an efficient synthetic method of carbazole derivatives from readily available N-arylnaphthalen-2-amines and quinone esters catalyzed by Brønsted acid. With this strategy, a series were obtained in good to excellent yields (76 >99) under mild conditions. Large scale reaction illustrated the utility protocol. Meanwhile, C-N axially chiral also constructed moderate (36-89% yield) with atroposelectivities (44-94% ee) using phosphoric acid as catalyst, which provides novel strategy for atroposelective construction compounds new member atropisomers.

Language: Английский

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Regioselective Synthesis of Polysubstituted Carbazoles from Indoles and Simple 1,4‐Dicarbonyl Compounds

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 884 - 891

Published: Jan. 3, 2024

Abstract Polysubstituted carbazoles were efficiently synthesized through direct benzannulation reaction between 1,4‐dicarbonyl compounds and indoles with catalytic amount of inexpensive zirconium(IV) chloride. This transformation proved to be regioselective furnishes 1,4‐disubstituted 1,2,4‐trisubstituted yields ranging from 26% 91% broad substrate scope. Moreover, this protocol benefits using readily accessible starting materials without the need their pre‐functionalization. The synthetic utility products was exemplified by functionalization an iodocarbazole means Suzuki‐Miyaura reactions synthesis a 3‐deaza‐derivative natural product canthin‐6‐one.

Language: Английский

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Pd/Cu-cocatalyzed multi-site functionalization of in-situ generated alkenes toward carbazole-based aggregation-induced emission luminogens

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2025, Volume and Issue: 69, P. 176 - 184

Published: Feb. 1, 2025

Language: Английский

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Fluorescence property and multifaceted applications of an aggregation-induced emission organic small molecule multifunctional material

Journal of Luminescence, Journal Year: 2025, Volume and Issue: unknown, P. 121202 - 121202

Published: March 1, 2025

Language: Английский

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Cascade Benzannulation Approach for the Syntheses of Lipocarbazoles, Carbazomycins, and Related Alkaloids

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(6), P. 4343 - 4359

Published: March 7, 2022

Herein, a state-of-the-art one-pot cascade benzannulation technique for the efficacious synthesis of valuable 3-hydroxy-2-methyl carbazoles, linchpin more than 25 carbazole-based alkaloids, is unveiled from readily affordable fundamental commodities. The key step this strategy gaining aromaticity by site-selective elimination hydroxyl group controlled nucleophilicity indole ring. present shows excellent functional tolerance with broad substrate scope. utility convenient approach was appealingly exemplified via concise total syntheses 10 alkaloids possessing significant biological activities and thus medicinal importance.

Language: Английский

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Construction of carbazole-based unnatural amino acid scaffolds via Pd(ii)-catalyzed C(sp³)–H functionalization

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(21), P. 4391 - 4414

Published: Jan. 1, 2022

Synthesis of racemic and enantiopure carbazole-based unnatural amino acid motifs was accomplished via diastereoselective Pd( ii )-catalyzed β-C(sp 3 )–H functionalization.

Language: Английский

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Iodine-Catalyzed Annulation Reaction of Ortho-Formylarylketones with Indoles: A General Strategy for the Synthesis of Indolylbenzo[b]carbazoles

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3666 - 3677

Published: March 8, 2023

The iodine-catalyzed cascade reaction of ortho-formylarylketones with indoles for the synthesis indolylbenzo[b]carbazoles is reported. initiated in presence iodine by two successive nucleophilic additions an aldehyde group ortho-formylarylketones, and ketone does not undergo a addition only involves Friedel-Crafts-type cyclization. A variety substrates are tested, efficiency this demonstrated gram-scale reactions.

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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Direct formation of 4,5-disubstituted carbazoles via regioselective dilithiation

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(59), P. 7252 - 7255

Published: Jan. 1, 2021

The simple combination of a bulky TIPS group on nitrogen and C–H activation using nBuLi–TMEDA allows direct functionalization the hindered bay region carbazole.

Language: Английский

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