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

Organic Letters, Год журнала: 2023, Номер 25(23), С. 4298 - 4302

Опубликована: Июнь 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.

Язык: Английский

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Rh(iii)-catalyzed C(sp²)–H functionalization/[4+2] annulation of oxadiazolones with iodonium ylides to access diverse fused-isoquinolines and fused-pyridines

Chemical Communications, Год журнала: 2024, Номер 60(51), С. 6560 - 6563

Опубликована: Янв. 1, 2024

A Rh( iii )-catalyzed C–H/N–H [4+2] annulation of oxadiazolones with iodonium ylides was developed, which afforded a series fused-isoquinolines and fused-pyridines.

Язык: Английский

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Rh(III)-Catalyzed [4 + 1] Annulation of Benzamides with Vinyl Cyclic Carbonates for the Synthesis of Isoindolinones

Organic Letters, Год журнала: 2024, Номер 26(7), С. 1304 - 1309

Опубликована: Фев. 8, 2024

A Rh(III)-catalyzed C–H bond activation and subsequent [4+1] annulation of benzamides with vinyl cyclic carbonates have been developed for the synthesis isoindolinones, in which electron-rich alkenes could serve as one-carbon units. This reaction proceeds smoothly high regioselectivity under oxidant- silver-free conditions exhibits broad substrate scope functional group tolerance including some biological active materials. The scale-up derivatizations product further demonstrate potential synthetic utility this transformation.

Язык: Английский

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Rh(III)-Catalyzed Fabrication of [4,3,1]-Bridged Azaheterocycles using Quinone Monoacetals

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 5, 2025

A rhodium-catalyzed annulation strategy for the fabrication of cyclohexanone-bridged indazolones and other related diazole-ones diazine-ones was established using quionone monoacetals under mild conditions. On hand, use 4-hydroxy-4-methylcyclohexa-2,5-dienone optimized Rh-conditions produced an ortho-CAr-arylated product in moderate reactivity. Mechanistic studies suggested that coupling proceeded via one-pot C-H activation-Michael/hetero-Michael additions into enone moiety. Interestingly, [4,3,1]-bridged-1,2-dihydro-3H-indazol-3-ones underwent unexpected migratory aromatization acidic condition to produce 3-hydroxy-14H-benzo[c]indazolo[1,2-a]cinnolin-14-ones high yields.

Язык: Английский

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Catalyst-Controlled C–H Allylation and Annulation of 2-Aryl Quinazolinones with 2-Methylidene Cyclic Carbonate

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13315 - 13326

Опубликована: Сен. 5, 2023

The site-selective modification of quinazolinone as a privileged bicyclic N-heterocycle is an attractive topic in medicinal chemistry and material science. We herein report the ruthenium(II)-catalyzed C-H allylation 2-aryl quinazolinones with 2-methylidene cyclic carbonate. In addition, tandem annulation are achieved under rhodium(III) catalysis, resulting formation tetracyclic including tertiary carbon center. Post-transformations synthesized products demonstrate potential developed methodology. A series mechanistic investigations were also performed.

Язык: Английский

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Construction of Diversified Penta‐Spiro‐Heterocyclic and Fused‐Heterocyclic Frameworks with Potent Antitumor Activity

Chemistry - A European Journal, Год журнала: 2023, Номер 29(54)

Опубликована: Июнь 28, 2023

Multiple-spiro/fused-heterocyclic frameworks containing indazolone are structurally unique and represent a class of potentially dominant skeletons. In this work, we successfully fulfilled Rh(III)-catalyst mediated substrate- pH- controlled strategies to construct four novel types complicated penta-spiro/fused-heterocyclic via C-H activation/[4+1] [4+2] annulation cascades. This method had mild reaction conditions, broad scope substrates, moderate good yields, valuable applications, which could realize for the first time generation di-spiro-heterocyclic multiple fused-heterocyclic products with structures. More importantly, spiro[cyclohexane-indazolo[1,2-a]indazole] scaffold constructed by exhibited potent antitumor activity against variety refractory solid tumors hematological malignancies in vitro. Overall, our work provided new insights into construction complex diverse spiro/fused-heterocyclic systems offered lead compounds discovery drugs.

Язык: Английский

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Rhodium‐Catalysed Selective C−H Allylation of 1H‐Indazoles with Vinylethylene Carbonate: Easily Introducing Allylic Alcohol

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(40)

Опубликована: Авг. 22, 2023

Abstract An efficient rhodium(III)‐catalysed C−H activation of 3‐aryl‐1‐ H ‐indazoles with easily available vinylethylene carbonate has been reported. A series allyl alcohol substituted were obtained broad functional groups tolerance and favourable stereoselectivity. Notably, C−O bonds selectively activated in “one pot” manner, releasing CO 2 as the sole by‐product avoiding external oxidant. This protocol provides a powerful approach for post stage allylation indazole‐based substrates.

Язык: Английский

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Synthesis of Bridged Cycloisoxazoline Scaffolds via Rhodium-Catalyzed Coupling of Nitrones with Cyclic Carbonate

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16330 - 16339

Опубликована: Ноя. 15, 2023

Bridged isoxazolidines were synthesized via Rh(III)-catalyzed C-H allylation of α-aryl nitrones with 5-methylene-1,3-dioxan-2-one. The nitrone group serves as a directing and 1,3-dipole in the activation/[3 + 2] cycloaddition cascade, exhibiting excellent chemo- stereoselectivity along good functional compatibility. resulting skeletal structure was conveniently modified to produce range important chemical frameworks, protocol applied biologically active molecules.

Язык: Английский

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Theoretical investigation of Cp*Rh(III)-catalyzed allylation and cyclization reactions of 1-arylindazolones with carbonates

Chemical Physics Letters, Год журнала: 2024, Номер 848, С. 141395 - 141395

Опубликована: Июнь 4, 2024

Язык: Английский

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Rh(III)-catalyzed [4 + 1] annulation of 1-arylindazolones with alkynyl cyclobutanols: access to indazolo[1,2-a]indazolones

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(32), С. 6500 - 6505

Опубликована: Янв. 1, 2024

A convenient and efficient synthesis of structurally diverse indazolo[1,2- a ]indazolones via Rh( iii )-catalyzed [4 + 1] annulation 1-arylindazolones with alkynyl cyclobutanols has been achieved by combining C–H C–C bond cleavage.

Язык: Английский

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